Methylamine → 5-fluoro-N-methyl-2-nitroaniline

HRID 1430399Notes

Reaction equation

HRID 1430399 reaction equation
[CH3:1][NH2:2].F[C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[N+:11]([O-:13])=[O:12]>CO>[F:10][C:8]1[CH:7]=[CH:6][C:5]([N+:11]([O-:13])=[O:12])=[C:4]([CH:9]=1)[NH:2][CH3:1]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 679672,4-Difluoronitrobenzene

Product 1

HCID 229057745-fluoro-N-methyl-2-nitroanilineYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

An aqueous solution of 40% methyl amine (61 mL, 0.71 mol) was added dropwise to a methanol solution (200 mL) of 2,4-difluoronitrobenzene (46.7 g, 0.29 mol) under ice cooling, and the mixture was stirred for 1 hour under the same temperature. The reaction solution was poured into ice water. Precipitated crystals were collected by filtration, followed by washing with water. The resulting crystals were dried at 50° C., thereby obtaining 47.6 g of a yellow, powdery target compound (yield: 95%).

Workup

  1. customPrecipitated crystals
  2. filtrationwere collected by filtration
  3. washby washing with water
  4. customThe resulting crystals were dried at 50° C.

Sources & evidence

ORD record
ord-2bd870b8d0c641ecb21d08a7c687a969
Source dataset
uspto-grants-2015_01
Patent number
US08940889B2

Reaction notes

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