Ammonium Hydroxide → 6-Carbamoylpyridine-2-carboxylic acid

HRID 1397289Notes

Reaction equation

HRID 1397289 reaction equation
C([O:8][C:9]([C:11]1[N:16]=[C:15]([C:17]([OH:19])=[O:18])[CH:14]=[CH:13][CH:12]=1)=O)C1C=CC=CC=1.C(Cl)(Cl)Cl.CO.[NH4+:26].[OH-]>>[C:9]([C:11]1[N:16]=[C:15]([C:17]([OH:19])=[O:18])[CH:14]=[CH:13][CH:12]=1)(=[O:8])[NH2:26]

Participants

4

Reactant 3

HCID 14923Ammonium HydroxideHCID 153299296-((Benzyloxy)carbonyl)picolinic acidHCID 21584188Chloroform methanol

Product 1

HCID 186766986-Carbamoylpyridine-2-carboxylic acidYield 94%

Procedure

A solution of 6-((benzyloxy)carbonyl)picolinic acid (3.0 g, 11.7 mmol) in saturated NH4OH (100 mL) was heated in a sealed tube at 90° C. for 6 h and monitored by TLC (CHCl3/MeOH 8:2 v/v). The reaction mixture was evaporated to dryness to get the 6-carbamoylpicolinic acid (1.8 g, yield 94%) as a white solid, which was carried through without further purification. MS (ESI) m/z: Calculated for C7H6N2O3: 166.04. found: 167.0 (M+H)+.

Workup

  1. customThe reaction mixture was evaporated to dryness

Sources & evidence

ORD record
ord-7042c9de5f974e19a8183d69b4054757
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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