Water → 4-Chloropyridine-2-carboxamide

HRID 709383Notes

Reaction equation

HRID 709383 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-fde8f6793d0d4c51bd1e47272532fd07
Source dataset
uspto-grants-2015_11
Patent number
US09181188B2

Reaction notes

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