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

HRID 1085475Notes

Reaction equation

HRID 1085475 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-8eea6df418b9460683a2c33e5dd1770c
Source dataset
uspto-grants-1991_04
Patent number
US05010086

Reaction notes

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