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

Participants

Role	Name	HCID	Charge
Reactant	Acetyl chloride	HCID 6367	—
Reactant	Triethylamine	HCID 8471	—
Reactant	2-(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-one	HCID 66607288	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	N-(5-Fluoro-2-oxo-2,3-dihydro-1H-indol-6-yl)acetamide	HCID 45118150	100.1%

Reaction Conditions

Temperature	0 °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 triethylamine (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

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08012966B2
Source dataset	uspto-grants-2011_09
ORD ID	ord-c227ea8be2da4d62be64e61e9d0a28b7
Source note	uspto-grants-2011_09