N-(4-chlorophenyl)formamide → HCID 58026188, compound

HRID 1514358Notes

Reaction equation

HRID 1514358 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH:11]=O)=[CH:6][CH:5]=1.[F:13][C:14]1[CH:19]=[CH:18][CH:17]=C(F)[N:15]=1>CN(C)C=O>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[CH:17]=[CH:18][CH:19]=[C:14]([F:13])[N:15]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 17475N-(4-chlorophenyl)formamideHCID 24758Sodium hydrideHCID 739342,6-Difluoropyridine

Product 1

HCID 58026188HCID 58026188, compoundYield 104%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (1.2 g, 30.9 mmol) was added to a solution of N-(4-chloro-phenyl)-formamide (4 g, 25.7 mmol) in N,N-dimethylformamide (40 mL) and stirred for 15 minutes. 2,6-Difluoropyridine (2.96 g, 25.7 mmol) was added, the reaction mixture was stirred at 70° C. overnight and poured into a stirred ice-water solution. The resulting participate was filtrated off and dried to give (4-chloro-phenyl)-(6-fluoro-pyridin-2-yl)-amine (5.95 g) as the crude product. The crude product was used without further purification.

Workup

  1. stirringthe reaction mixture was stirred at 70° C. overnight
  2. filtrationThe resulting participate was filtrated off
  3. customdried

Sources & evidence

ORD record
ord-a8508c360c564396943f549647b9497a
Source dataset
uspto-grants-2012_07
Patent number
US08222262B2

Reaction notes

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