Acetyl chloride → N-(2-oxoindolin-5-yl)acetamide

HRID 1811204Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.[C:12](Cl)(=[O:14])[CH3:13].C(OCC)(=O)C>O1CCCC1>[O:11]=[C:6]1[CH2:5][C:4]2[C:8](=[CH:9][CH:10]=[C:2]([NH:1][C:12](=[O:14])[CH3:13])[CH:3]=2)[NH:7]1

Participants

Conditions

Temperature: -30 °C

Procedure

A stirred solution of 5-amino-1,3-dihydro-indol-2-one (3.5 g, 23.6 mmol, prepared according to U.S. Pat. No. 6,114,371) in 20 ml of tetrahydrofuran was added with tirethylamine (1.3 ml, 9 mmol). The solution was cooled down to −30° C. in an acetone-dry ice bath and added with acetyl chloride (1.3 ml, 9 mmol) dropwise. Upon the completion of the addition, the resulting mixture was stirred for 20 minutes at room temperature and added with ethyl acetate (20 ml) until precipitate was formed. The solid was filtered, washed with water (50 ml×3) and dried in vacuo to give N-(2-oxo-2,3-dihydro-1H-indol-5-yl)-acetamide (4 g, 88.9%) as a white solid.

Workup

additionUpon the completion of the addition
customwas formed
filtrationThe solid was filtered
washwashed with water (50 ml×3)
customdried in vacuo

Sources & evidence

ORD record: ord-cb8b9bfc88c7453caf7dafa73fe8bff2
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362251B2

Reaction notes

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