Ammonium Hydroxide → 4-Chloropyridine-2-carboxamide

HRID 493108Notes

Reaction equation

HRID 493108 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][N:6]=1)=O.[OH-].[NH4+:13]>CO>[Cl:11][C:9]1[CH:8]=[CH:7][N:6]=[C:5]([C:3]([NH2:13])=[O:2])[CH:10]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 820890Methyl 4-Chloropicolinate

Product 1

HCID 3035434-Chloropyridine-2-carboxamideYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Chloro-pyridine-2-carboxylic acid methyl ester (2) (500 mg, 3 mmol) was dissolved in MeOH (5 ml) and concentrated ammonium hydroxide (5 ml) was added. After 10 minutes, the reaction mixture was partitioned between ethyl acetate and brine. The ethyl acetate was washed with brine one additional time, and the solvents were removed under vacuum to yield the title product 3 (400 mg (85%), 2.5 mmol) as a white solid. 1H NMR (DMSO-d6): δ 8.64 (d, J=5.3 Hz, 1H), 8.22 (bs, 1H), 8.03 (d, J=1.9 Hz, 1H), 7.83 (bs, 1H), 7.68 (dd, J=5.3 Hz, 1.9 Hz, 1H). MS (ESI-POS): [M+H]+=157.

Workup

  1. customthe reaction mixture was partitioned between ethyl acetate and brine
  2. washThe ethyl acetate was washed with brine one additional time
  3. customthe solvents were removed under vacuum

Sources & evidence

ORD record
ord-fe5c27129a5642c2a73881b881b4eb3d
Source dataset
uspto-grants-2009_05
Patent number
US07534796B2

Reaction notes

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