2-Nitroaniline → Benzenemethanamine, 4-fluoro-N-(2-nitrophenyl)-

HRID 2210829Notes

Reaction equation

HRID 2210829 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].[F:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16]Cl)=[CH:14][CH:13]=1>C(C(C)=O)C>[F:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16][NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N+:1]([O-:3])=[O:2])=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 69462-NitroanilineHCID 96024-Fluorobenzyl chloride

Product 1

HCID 11311160Benzenemethanamine, 4-fluoro-N-(2-nitrophenyl)-

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

56 g N-(4-fluorobenzyl) 2-nitroaniline are reduced in the presence of 34 g of 5% palladized charcoal into methanol (560 ml) using a stream of hydrogen at room temperature and normal pression. After achievement of the reaction, the mixture is washed with nitrogen, filtered on clay (Trade Mark Celite) and concentrated to dryness. The residue is recrystallized from isopropyl ether. The desired N-substituted phenylene diamine, is thus obtained recovered weight: 38.5 g. The starting material N-(4-fluorobenzyl) 2-nitroaniline is prepared by alkylating the 2-nitroaniline by means of 4-fluorobenzyl chloride in the methyl ethyl ketone.

Workup

  1. customrecovered weight

Sources & evidence

ORD record
ord-71b6a4a453dd4985aa36bbdea00cf675
Source dataset
uspto-grants-1995_10
Patent number
US05461059

Reaction notes

Loading…