Water → 2-Chloro-1-(5-chloro-3-phenyl-2,3-dihydro-1H-indol-1-yl)ethan-1-one

HRID 262294Notes

Reaction equation

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

Participants

Conditions

Temperature: 15 °C

Procedure

2.7 G of N-chloracetyl-3-phenylindoline was added with vigorous stirring to a solution of 0.77 g of chlorine in 10 ml of glacial acetic acid which had been cooled to 15° C. The temperature of the mixture which rose to 33° C. was cooled down to room temperature and the mixture stirred for a further hour. The resulting solution was poured into 100 ml of cold water. The liquid was decanted from the gummy residue, which was subsequently crystallized from ethanol to give 1.9 g of crystalline N-chloracetyl-3-phenyl-5-chloroindoline having a melting point of 107°-9° C.

Workup

customrose to 33° C.
temperaturewas cooled down to room temperature
customThe liquid was decanted from the gummy residue, which
customwas subsequently crystallized from ethanol

Sources & evidence

ORD record: ord-5cdde8e2f88e4b48b055b916347a53d8
Source dataset: uspto-grants-1979_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04153789

Reaction notes

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