2-Chloro-5-nitroaniline → N-(3-chloro-5-trifluoromethyl-2-pyridyl)-2-chloro-5-nitroaniline

HRID 1708935Notes

Reaction equation

HRID 1708935 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:3]=1[NH2:4].Cl[C:13]1[C:18]([Cl:19])=[CH:17][C:16]([C:20]([F:23])([F:22])[F:21])=[CH:15][N:14]=1>[Cu]>[Cl:19][C:18]1[C:13]([NH:4][C:3]2[CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[CH:7]=[CH:8][C:2]=2[Cl:1])=[N:14][CH:15]=[C:16]([C:20]([F:22])([F:21])[F:23])[CH:17]=1

Participants

4

Reactant 2

HCID 226912-Chloro-5-nitroanilineHCID 1122342,3-Dichloro-5-(trifluoromethyl)pyridine

Product 1

HCID 23038935N-(3-chloro-5-trifluoromethyl-2-pyridyl)-2-chloro-5-nitroanilineYield 22.7%

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Procedure

3.4 g (0.02 mol) of 2-chloro-5-nitroaniline, 8.6 g (0.04 mol) of 2,3-dichloro-5-trifluoromethylpyridine and 400 mg of copper powder are maintained at 230° C. overnight in a small bomb tube (25 ml). After cooling, the crude product is purified by column chromatography (silica gel, petroleum ether:methylene chloride=6:1), affording 1.6 g of N-(3-chloro-5-trifluoromethyl-2-pyridyl)-2-chloro-5-nitroaniline in the form of a yellow powder (m.p. 122°-124° C.).

Workup

  1. temperatureAfter cooling
  2. customthe crude product is purified by column chromatography (silica gel, petroleum ether:methylene chloride=6:1)

Sources & evidence

ORD record
ord-e982caaf77b44ec2b2a74440724be21d
Source dataset
uspto-grants-1990_08
Patent number
US04946854

Reaction notes

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