Trifluoroacetic acid → 5-(2-Chloroethyl)-6-chlorooxindole

HRID 1724631Notes

Reaction equation

C([SiH](CC)CC)C.[Cl:8][CH2:9][C:10]([C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][C:20]=1[Cl:21])[NH:17][C:16](=[O:22])[CH2:15]2)=O.FC(F)(F)C(O)=O>>[Cl:8][CH2:9][CH2:10][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][C:20]=1[Cl:21])[NH:17][C:16](=[O:22])[CH2:15]2

Participants

Reactant 3

HCID 6422Trifluoroacetic acid

HCID 12052Triethylsilane

HCID 37309465-chloroacetyl-6-chlorooxindole

Product 1

HCID 106094745-(2-Chloroethyl)-6-chlorooxindoleYield 92.3%

Conditions

Temperature: 42.5 °C

Procedure

Triethylsilane (57.2 gm) was added slowly to the reaction mixture of 5-(2-Chloro acetyl)-6-chloro oxindole (50.0 gm) and trifluoroacetic acid (175 mL) below the temperature of 45° C. The reaction was maintained at 40-45° C. for 6 hours. The reaction mass was cooled to 0° C. to −5° C. and maintained stirring for 90 minutes. The separated solid was filtered and washed with water (50 mL). Then the wet compound was further slurred in water (250 mL) for 90 minutes. The resultant solid was filtered, washed with water (50 mL) and dried at a temperature of 70-75° C. to afford 5-(2-chloroethyl)-6-chloro oxindole (43.5 gm).

Workup

temperatureThe reaction mass was cooled to 0° C. to −5° C.
temperaturemaintained
filtrationThe separated solid was filtered
washwashed with water (50 mL)
waitThen the wet compound was further slurred in water (250 mL) for 90 minutes
filtrationThe resultant solid was filtered
washwashed with water (50 mL)
customdried at a temperature of 70-75° C.

Sources & evidence

ORD record: ord-d34c50d2d2594001ba6c7509b06fb4ac
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07488729B2

Reaction notes

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