Oxalyl chloride → 2-(1-(4-chlorobenzyl)-1H-indol-3-yl)-2-oxo-acetyl chloride

HRID 1611404Notes

Reaction equation

[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[CH:8]2)=[CH:4][CH:3]=1.[C:18](Cl)(=[O:22])[C:19]([Cl:21])=[O:20]>C(OCC)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([C:18](=[O:22])[C:19]([Cl:21])=[O:20])=[CH:8]2)=[CH:16][CH:17]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 1-(4-chlorobenzyl)-1H-indole (2.0 g) in dry ethyl ether (5 ml) kept under stirring and cooled at 0° C. is dropwise added with a solution of oxalyl chloride (0.85 ml) in dry ethyl ether (2 ml). After completion of the addition, the mixture is left at room temperature for 2h. The separated solid is recovered by filtration, washed with dry ethyl ether and dried under vacuum at 40° C. to give 2-(1-(4-chlorobenzyl)-1H-indol-3-yl)-2-oxo-acetyl chloride (1.64 g).

Workup

additionAfter completion of the addition
filtrationThe separated solid is recovered by filtration
washwashed with dry ethyl ether
customdried under vacuum at 40° C.

Sources & evidence

ORD record: ord-f2c332d715d34f19be366fad1dc67ea6
Source dataset: uspto-grants-2006_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06987122B2

Reaction notes

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