Ammonia → 3-Chloro-2-methyl-6-nitroaniline

HRID 327448

Reaction equation

HRID 327448 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[C:3]=1[CH3:12].[NH3:13]>>[Cl:11][C:4]1[C:3]([CH3:12])=[C:2]([NH2:13])[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 971552,6-Dichloro-3-nitrotoluene

Product 1

HCID 129530203-Chloro-2-methyl-6-nitroanilineYield 76%

Conditions

Temperature
130 °C

Procedure

A suspension of 2,6-dichloro-3-nitrotoluene (6.0 g, 29 mmol) in 50% methanolic ammonia (60 mL) was stirred at 130° C. (340 lb pressure) for 18 hours. The autoclave was cooled to -30° C., opened, and the precipitate was filtered off and washed with methanol to give 4.14 g (76%) of 3-chloro-2-methyl-6-nitrobenzenamine.

Workup

  1. temperatureThe autoclave was cooled to -30° C.
  2. filtrationthe precipitate was filtered off
  3. washwashed with methanol

Sources & evidence

ORD record
ord-6a783ee54f534c5382fab3da4c85a8fe
Source dataset
uspto-grants-1993_12
Patent number
US05273975

Linked notes

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