2-Chloroaniline → 1-(2-Chlorophenyl)pyrrolidin-2-one

Reaction equation

[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[C:9]1(=O)[O:13][CH2:12][CH2:11][CH2:10]1>>[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[N:4]1[CH2:9][CH2:10][CH2:11][C:12]1=[O:13]

Participants

Reactant 2

HCID 72402-Chloroaniline

HCID 7302Gamma-Butyrolactone

Product 1

HCID 41405531-(2-Chlorophenyl)pyrrolidin-2-oneYield 25.4%

Procedure

Following example 19, 12.57 g (0.1M) of 2-chloroaniline and 9.5 g (0.11M) of γ-butyrolactone were heated for 48 hours. The excess starging materials were removed at 50°-80°/0.3 mm. Distillation of the residue gave 4.9 g (25%) of product (45% based on recovered 2-chloroaniline); b.p. 150°-155°/0.3-0.4 mm.

Workup

temperaturewere heated for 48 hours
customThe excess starging materials were removed at 50°-80°/0.3 mm
distillationDistillation of the residue

Sources & evidence

ORD record: ord-d9f58c0facda44309451c23641721e5a
Source dataset: uspto-grants-1984_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04424210

Reaction notes

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