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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1811200Generated: October 31, 2026

Acetyl chloride → N-(5-Fluoro-2-oxo-2,3-dihydro-1H-indol-6-yl)acetamide

https://huagongshe.com/reaction/1811200

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAcetyl chlorideHCID 6367—
Reactant2-(6-Amino-5-fluoro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-5-(2-diethylamino-ethyl)-3-methyl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-4-oneHCID 66607288—
SolventTetrahydrofuranHCID 8028—
ProductN-(5-Fluoro-2-oxo-2,3-dihydro-1H-indol-6-yl)acetamideHCID 45118150100.1%

Reaction Conditions

Temperature0 °C

Reaction Steps

A stirred solution of 6-amino-5-fluoro-1,3-dihydro-indol-2-one (1.0 g, 6 mmol) obtained from Example 7 in 30 ml of tetrahydrofuran was added with tirethylamine (1.3 ml, 9 mmol). The solution was cooled down to 0° C. in an ice-water bath and added with acetyl chloride (1.3 ml, 9 mmol) dropwise. Upon the completion of the addition, the resulting mixture was heated to reflux for 1.5 hours and cooled until precipitate was formed. The solid was filtered, washed with water (50 ml×3) and dried in vacuo to give N-(5-fluoro-2-oxo-2,3-dihydro-1H-indol-6-yl)-acetamide (1.25 g, 99%) as a white solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08362251B2
Source datasetuspto-grants-2013_01
ORD IDord-bd39b971f32e48b8a4a2c7984f460e60
Source noteuspto-grants-2013_01