Chloroacetone → N-(3-nitrophenyl)-N-(2-oxo-propyl)-formamide

HRID 1835476Notes

Reaction equation

HRID 1835476 reaction equation
[CH:1]([NH:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[CH:5]=1)=[O:2].[H-].[Na+].Cl[CH2:16][C:17](=[O:19])[CH3:18]>CN(C)C=O.C(OCC)(=O)C.O>[N+:10]([C:6]1[CH:5]=[C:4]([N:3]([CH2:16][C:17](=[O:19])[CH3:18])[CH:1]=[O:2])[CH:9]=[CH:8][CH:7]=1)([O-:12])=[O:11]

Participants

7

Reactant 3

HCID 6571ChloroacetoneHCID 24758Sodium hydrideHCID 5971093'-Nitroformanilide

Product 1

HCID 23503669N-(3-nitrophenyl)-N-(2-oxo-propyl)-formamideYield 21%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of N-formyl-3-nitroaniline (1.0 g) in N,N-dimethylformamide (10 ml) was added sodium hydride (60% dispersion in mineral oil, 264 mg), and the mixture was stirred for 20 minutes under nitrogen atmosphere. After a solution of 1-chloropropan-2-one (0.573 ml) in N,N-dimethylformamide (5 ml) was added dropwise to the mixture, the mixture was stirred for 2 hours and diluted with ethyl acetate and water. The separated organic layer was washed with brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified with a silica gel column chromatography eluting with 2% methanol in dichloromethane to give N-(3-nitrophenyl)-N-(2-oxo-propyl)-formamide (280 mg, 21.0%).

Workup

  1. stirringthe mixture was stirred for 2 hours
  2. washThe separated organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was purified with a silica gel column chromatography
  6. washeluting with 2% methanol in dichloromethane

Sources & evidence

ORD record
ord-374c63c7b51c4e118b78249ac2cb63d0
Source dataset
uspto-grants-2004_08
Patent number
US06770667B1

Reaction notes

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