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

HRID 353473Notes

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 to 0° C. is added drop by drop with a solution of oxalyl chloride (0.85 ml) in dry ethyl ether (2 ml). Afterwards the reaction is left at room temperature for 2 h. 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

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

Sources & evidence

ORD record: ord-c90857d6863b4988a6dbd9ba35d41fdf
Source dataset: uspto-grants-2004_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06753342B2

Reaction notes

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