5-Chloro-4-fluoro-N-methyl-2-nitrobenzenamine → HCID 89093530, compound

HRID 1048971Notes

Reaction equation

HRID 1048971 reaction equation
[Cl:1][C:2]1[C:3]([F:13])=[CH:4][C:5]([N+:10]([O-])=O)=[C:6]([CH:9]=1)[NH:7][CH3:8]>CO.[Ni]>[Cl:1][C:2]1[CH:9]=[C:6]([NH:7][CH3:8])[C:5]([NH2:10])=[CH:4][C:3]=1[F:13]

Participants

4

Reactant 1

HCID 666842915-Chloro-4-fluoro-N-methyl-2-nitrobenzenamine

Product 1

HCID 89093530HCID 89093530, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A stifled solution of 5-chloro-4-fluoro-N-methyl-2-nitroaniline (8; 1.5 g, 0.0078 mol) in MeOH (20 ml) was hydrogenated using Raney Ni for 6 h at room temperature. The reaction was filtered through CELITE® and the filter bed was thoroughly washed with MeOH. The resulting solution was concentrated to provide 5-chloro-4-fluoro-N1-methylbenzene-1 2-diamine as a brownish solid. 1H NMR (400 MHz, DMSO-d6), δ: 6.49-6.47 (d, 11.6 Hz, 1H), 6.30-6.28 (d, J=7.6 Hz, 1H) 4.96 (bs, 2H), 4.74 (bs, 1H), 2.67 (s, 3H). MS (M+1): 175.1.

Workup

  1. customfor 6 h
  2. customat room temperature
  3. filtrationThe reaction was filtered through CELITE®
  4. washthe filter bed was thoroughly washed with MeOH
  5. concentrationThe resulting solution was concentrated

Sources & evidence

ORD record
ord-baa4febbe0414835ba596fa452e731d5
Source dataset
uspto-grants-2016_07
Patent number
US09382226B2

Reaction notes

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