Organic Compound Synthesis

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Questions and Answers

Which of the following is a substrate used in the production of nicotinic acid?

  • 4-Picoline
  • Salol
  • Pyramidonum
  • 3-Picoline (correct)

What type of reaction is used to obtain substituted derivatives of isonicotinic acid from 4-picoline?

  • Oxidation
  • Esterification (correct)
  • Reduction
  • Hydrolysis

Salicylamide is best described as which of the following?

  • Salt of salicylic acid
  • Amide of salicylic acid (correct)
  • Ether of salicylic acid
  • Ester of salicylic acid

Which of the following reagents is reacted with 4-amino-1,5-dimethyl-2-phenylpyrazol-3-one to synthesize Pyramidonum?

<p>Dimethylamine (D)</p> Signup and view all the answers

In the synthesis of derivatives of pyrazolidinedione, what are the primary starting materials?

<p>Esters of malonic acids and hydrazines (C)</p> Signup and view all the answers

Luminal, a derivative of barbituric acid, is synthesized through the condensation of diethyl ester with which other reactant?

<p>Urea (A)</p> Signup and view all the answers

What is the immediate precursor in the synthesis of p-nitrofenetol?

<p>p-Nitrophenol (D)</p> Signup and view all the answers

Which compound is typically used as the starting material for synthesizing derivatives of p-aminophenol?

<p>p-Nitrophenol (C)</p> Signup and view all the answers

What is the starting material for the production of derivatives of p-aminobenzoic acid?

<p>p-Nitrotoluene (D)</p> Signup and view all the answers

What is the role of pyridine in the condensation of ASC or p-chlorosulfonylphenylurethane with amines to produce sulfonamides?

<p>Acceptor of hydrogen chloride (C)</p> Signup and view all the answers

Which class of compounds serves as the substrate for most sulfonamide syntheses?

<p>p-Acetylaminobenzenesulfonyl chloride (C)</p> Signup and view all the answers

2-aminothiazole, a key intermediate in the synthesis of sulfathiazole, can be synthesized from which of the following?

<p>Aldehydes (A)</p> Signup and view all the answers

What other reactant is needed to produce Benactizin from benzaldehyde?

<p>2-Diethylaminoethyl chloride (D)</p> Signup and view all the answers

Which compound is a key intermediate in the synthesis of 1,1-diphenylo-2-piperydynopropanol (Jessical)?

<p>Propiophenone (B)</p> Signup and view all the answers

What happens to phenylacetic acid to get phenylacetylonitrile?

<p>Hydration (D)</p> Signup and view all the answers

Esters of which acid are key intermediates in the synthesis of Methylphenidate?

<p>Phenyl-2-piperidyl-2-acetic acid (D)</p> Signup and view all the answers

Amphetamine is synthesized from which of the following?

<p>Phenylacetylonitrile (A)</p> Signup and view all the answers

In the synthesis of Bemegride, what is a key starting material?

<p>Ethyl methyl ketone (D)</p> Signup and view all the answers

Which type of substituted benzene is a precursor to ethacridine lactate production?

<p>Chlorobenzene (C)</p> Signup and view all the answers

What is the role of chlorosulfonic acid in saccharin synthesis?

<p>Sulfonating agent (A)</p> Signup and view all the answers

Flashcards

Nicotinic Acid Substrates

Substrates for obtaining nicotinic acid and its derivatives include picoline, quinoline bases, quinoline, 3-picoline, 5-ethyl-2-methylpyridine, and nicotine; oxidation with sodium or potassium permanganate.

Ethyl Nicotinate Synthesis

Reacting 3-picoline with sulfuric acid yields nicotinic acid which then reacts with ethanol to form ethyl nicotinate.

Uses of ethyl nicotinate

Ethyl nicotinate reacts with diethylamide to form nicetamid, or with ethanolamine, to form cholamid

Isonicotinic Acid Synthesis

4-Picoline reacts with potassium permanganate to produce isonicotinic acid; further reactions convert it to methyl isonicotinate and iproniazid.

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Salol Synthesis

Salol is produced from salicylic acid using the Kolbe-Schmitt reaction; it's phenyl salicylate.

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Creation of salicylic acid

Hydrolyzing phenyl salicylate or methyl salicylate with a base yields salicylic acid

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PAS Synthesis

PAS is p-aminosalicylic acid, synthesized from nitrobenzene via reduction and carboxylation.

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Pyrazolone Derivatives

Derivatives of pyrazolone include (a) 1,5-dimethyl-2-phenylpyrazol-3-one (Antipyrine) and (b) 1,5-dimethyl-4-dimethylamino-2-phenylpyrazol-3-one (Pyramidone).

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Antipyrine Synthesis

1,5-dimethyl-2-phenylpyrazol-3-one (Antipyrine) can be synthesized via multiple reactions from a substituted pyrazolone.

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Pyrazolidinedione Synthesis

Raw materials used include malonic acid esters with appropriate substitutions. Phenylhydrazine or N,N'-diphenylhydrazine.

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Barbituric Acid Synthesis

Derivatives of barbituric acid are obtained through condensation of malonic esters with urea.

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Veronal

Veronal is diethylbarbituric acid.

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p-Aminophenol Derivatives

Derivatives of p-aminophenol are obtained from p-nitrosophenol through nitrosation and oxidation, followed by reduction.

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p-Aminophenol Substrate

A substrate for synthesizing p-aminophenol derivatives is usually p-nitrophenol, obtained in situ through nitrosation and oxidation.

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Study Notes

  • These are study notes on various organic compounds and their synthesis, including pyridine derivatives, salicylic acid derivatives, pyrazolone derivatives, pyrazolidinedione derivatives, barbituric acid derivatives, p-aminophenol derivatives, p-aminobenzoic acid derivatives, sulfonamides, diphenylmethane derivatives, and others.

Pyridinecarboxylic Acid Derivatives

  • Includes nicotinic acid amide, diethylamide nicotinic acid, and hydroxymethylamide nicotinic acid.
  • Substrates for obtaining nicotinic acid and its derivatives: picoline, quinoline bases, ethyl-methylpyridine, and oxidation using potassium permanganate.
  • Isonicotinic acid derivatives are obtained from 4-picoline.

Salicylic Acid Derivatives

  • Salicylic acid derivatives are produced using the Kolbe-Schmitt method.
  • Includes phenyl salicylate, methyl salicylate, salicylamide.
  • PAS is para-aminosalicylic acid, which is 4-amino-2-hydroxybenzoic acid.

Pyrazolone and Pyrazolidinedione Derivatives

  • Includes 1,5-dimethyl-2-phenylpyrazol-3-one (Antipyrine) and 1,5-dimethyl-4-dimethylamino-2-phenylpyrazol-3-one (Pyramidone).
  • Starting materials are derivatives of pyrazolone-3 with ethyl acetoacetate and phenyllhydrazine.
  • Includes the synthesis of Antipyrine and Pyramidone from 1,5-dimethyl-2-phenyl-4-nitrosopyrazol-3-one.
  • Pyrazolidynodionu: Starting with esters derived from malonic acids.
  • Includes 2,4-diphenylpyrazolidine-3,5-dione, which is Osadryn and 4-butyl-1,2-diphenylpyrazolidine-3,5-dione, which is Butapirazol.

Barbituric Acid Derivatives

  • Obtained by condensing diethyl esters of appropriately substituted malonic acids with urea.
  • Includes Veronal, which is diethylbarbituric acid, and Luminal.

p-Aminophenol Derivatives

  • Synthesis typically uses p-nitrophenol, obtained from benzene which undergoes the process of nitrosation and oxidation of the resulting nitrosol.
  • Includes p-acetylaminopheol and paracetamol and p-phenetidine.

p-Aminobenzoic Acid Derivatives

  • p-Nitrotoluene is used to produce p-aminobenzoic acid derivatives.
  • Derivatives can be obtained through: oxidation to p-nitrobenzoic acid derivatives or reducing p-nitrotoluene to p-toluidine.
  • Examples include ethyl p-aminobenzoate (Anesthesin) and procaine.

Sulfonamides

  • Substrate for synthesizing sulfa drugs is chlorosulfonic acid, used on acetanilide to produce p-acetylaminobenzenesulfonyl chloride (ASC).
  • ASC or chlorosulfonylurethane is condensed with amines.
  • Includes sulfanilamide.
  • Derivatives: sulfacetamide
  • Contains 2-(p-aminobenzenesulfonamido) pyridine (sulfapyridine).

CD (Sulfonamides Continued)

  • 2-sulfanilamidothiazole (sulfathiazole).
  • Prepared using ASC, which is hydrolyzed partially in a previous acetylated step.
  • Reacting with 2-aminotiazole
  • Guanidine sulfanilamide (sulfaguanidine).

Diphenylmethane Derivatives

  • Synthesis
  • Chlorohydrate of diethylaminoethylic ester of benzilic acid - Benactyzine. substrate for the production of benzilic acid is benzaldehyde
  • Chlorohydrate of diethylaminoethylic ester of diphenylacetic kwasu- Vegantin.
  • Diethylaminoethylic ester for vegatnin, adiphanine, difectil, spasmolitin.
  • Morazone, pyrisal, are precursors for Diphenylmethane
  • 1,1-diphenyl-2-piperydynopropaned-Tussucal - starting chlorochloride propionylu

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