4-Nitroaniline → HCID 91989079, compound

HRID 350668Notes

Reaction equation

HRID 350668 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)([O-:3])=[O:2].[Cl:11][CH2:12][CH2:13][CH2:14][C:15]#[N:16]>C(OCC)(=O)C>[ClH:11].[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([N:8]2[CH2:12][CH2:13][CH2:14][C:15]2=[NH:16])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 74754-NitroanilineHCID 123364-Chlorobutyronitrile

Product 1

HCID 91989079HCID 91989079, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
190 °C

Procedure

A mixture of 40.0 g (290 mmol) of 4-nitroaniline and 40.0 ml (421 mmol) of 4-chlorobutyronitrile is heated at the boil (about 190° C.) for 30 minutes using a hot-air fan. The mixture is allowed to cool and is digested with ethyl acetate, giving 1-(4-nitrophenyl)pyrrolidin-2-ylideneamine, hydrochloride, as a brown solid, ESI 206.

Workup

  1. temperatureto cool

Sources & evidence

ORD record
ord-ecf242ec1037449f8b77fcb48eec4d07
Source dataset
uspto-grants-2007_02
Patent number
US07183277B2

Reaction notes

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