Ethanol → 2-Amino-6-methyl-5-phenylpyridine-3-carboxylic acid

HRID 1088672Notes

Reaction equation

HRID 1088672 reaction equation
Cl[C:2]1C(C#N)=[CH:6][C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:4]([CH3:16])[N:3]=1.[OH-:17].[NH4+:18].[CH2:19]([OH:21])[CH3:20]>C(O)(=O)C>[NH2:18][C:2]1[C:20]([C:19]([OH:17])=[O:21])=[CH:6][C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:4]([CH3:16])[N:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14923Ammonium HydroxideHCID 14763652-Chloro-6-methyl-5-phenylnicotinonitrile

Product 1

HCID 135028632-Amino-6-methyl-5-phenylpyridine-3-carboxylic acidYield 82%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
185 °C

Procedure

A mixture of 92.71 g 2-chloro-3-cyano-6-methyl-5-phenylpyridine, 1000 ml concentrated ammonium hydroxide and 400 ml ethanol was heated in an autoclave at 185° C. for 30 hours. The reaction mixture was cooled in ice, neutralized with acetic acid and stirred at room temperature for 2 hours. The solid product was collected, washed with water (800 ml) and a small amount of ethanol, and dried in a vacuum oven at 85° C. to give 75.61 g (82%) of 2-amino-6-methyl-5-phenyl-3-pyridinecarboxylic acid, m.p. 298-300° C.

Workup

  1. temperatureThe reaction mixture was cooled in ice
  2. customThe solid product was collected
  3. washwashed with water (800 ml)
  4. dry with materiala small amount of ethanol, and dried in a vacuum oven at 85° C.

Sources & evidence

ORD record
ord-e3b0f84d5da141d7bc42aed3655707a9
Source dataset
uspto-grants-1990_10
Patent number
US04963561

Reaction notes

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