1-Chloro-2-nitrobenzene → N-(4-methoxybenzyl)-2-nitroaniline

HRID 1722723Notes

Reaction equation

HRID 1722723 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[CH3:11][O:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][NH2:18])=[CH:15][CH:14]=1.C([O-])(=O)C.[NH4+]>>[CH3:11][O:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][NH:18][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[N+:8]([O-:10])=[O:9])=[CH:15][CH:14]=1

Participants

4

Reactant 3

HCID 69451-Chloro-2-nitrobenzeneHCID 754524-MethoxybenzylamineHCID 517165Ammonium Acetate

Product 1

HCID 2920606N-(4-methoxybenzyl)-2-nitroanilineYield 100%

Procedure

Reaction of 2-chloronitrobenzene (10 g, 63 mmole), 4-methoxybenzylamine (52.1 g, 380 mmole) and ammonium acetate (4.6 g) substantially as described in 1C above producted 15 g (100%) of title compound as orange crystals: mp 75°-78°.

Sources & evidence

ORD record
ord-bdb08fefc52a432190e4f36de432d1cf
Source dataset
uspto-grants-1989_08
Patent number
US04857540

Reaction notes

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