Water → 4-Chloropyridine-2-carboxamide

HRID 885094Notes

Reaction equation

HRID 885094 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]([O:11]C)=O)[CH:4]=1.[Cl-].[NH4+:14].CCOC(C)=O.O>N>[Cl:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]([NH2:14])=[O:11])[CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 16655470Methyl 4-chloropyridine-2-carboxylate--hydrogen chloride (1/1)

Product 1

HCID 3035434-Chloropyridine-2-carboxamideYield 214.4%

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

To a stirred mixture of methyl 4-chloro-2-pyridinecarboxylate hydrochloride (1.0 g, 4.81 mmol) dissolved in conc. aqueous ammonia (32 mL) was added ammonium chloride (96.2 mg, 1.8 mmol, 0.37 equiv.), and the heterogeneous reaction mixture was stirred at ambient temperature for 16 h. The reaction mixture was poured into EtOAc (500 mL) and water (300 mL). The organic layer was washed with water (2×300 mL) and a saturated NaCl solution (1×300 mL), dried (MgSO4), concentrated in vacuo to give 4-chloro-2-pyridinecarboxamide as a beige solid (604.3 mg, 80.3%): TLC (50% EtOAc/hexane) Rf 0.20; 1H-NMR (DMSO-d6) δ 8.61 (d, J=5.4 Hz, 1H), 8.20 (broad s, 1H), 8.02 (d, J=1.8 Hz, 1H), 7.81 (broad s, 1H), 7.76 to 7.73 (m, 1H).

Workup

  1. washThe organic layer was washed with water (2×300 mL)
  2. dry with materiala saturated NaCl solution (1×300 mL), dried (MgSO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-30d997d848bd47a6a283d836392bfdec
Source dataset
uspto-grants-2012_08
Patent number
US08242147B2

Reaction notes

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