Acetic Acid → 1H-Indole-1-acetic acid, 3-[(4-chlorophenyl)thio]-4,5,6,7-tetrahydro-4-(hydroxyimino)-2-methyl-

HRID 1516988Notes

Reaction equation

[OH-].[Na+].O.[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([S:11][C:12]2[C:20]3[C:19](=[N:21][OH:22])[CH2:18][CH2:17][CH2:16][C:15]=3[N:14]([CH2:23][C:24]([O:26]CC)=[O:25])[C:13]=2[CH3:29])=[CH:7][CH:6]=1.C(O)(=O)C>C(O)C>[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([S:11][C:12]2[C:20]3[C:19](=[N:21][OH:22])[CH2:18][CH2:17][CH2:16][C:15]=3[N:14]([CH2:23][C:24]([OH:26])=[O:25])[C:13]=2[CH3:29])=[CH:7][CH:6]=1

Participants

Conditions

Temperature: 40 °C

Procedure

Aqueous sodium hydroxide (1M, 10 mL, 10 mmol) and water (20 mL) were added to a stirred suspension of ethyl [3-(4-chloro-phenylsulfanyl)-4-(hydroxyimino)-2-methyl-4,5,6,7-tetrahydro-1H-indol-1-yl]acetate (4.0 g, 10.2 mmol) and ethanol 40 mL) and the mixture was warmed up to 40° C. After 1.5 h at this temperature, the reaction mixture was allowed to cool to r.t. and held overnight. The suspension was reheated to 33° C. and acetic acid (1.7 mL, 29.7 mmol) added to the resulting solution. The mixture was allowed to cool to r.t., the solid product was collected by filtration, washed with water (2×20 mL), then dried under vacuum at 30° C. to provide the title compound as a solid; 2.94 g (79%); purity by HPLC 98.9 area %

Workup

temperatureto cool to r.t.
waitheld overnight
customwas reheated to 33° C.
temperatureto cool to r.t.
filtrationthe solid product was collected by filtration
washwashed with water (2×20 mL)
customdried under vacuum at 30° C.

Sources & evidence

ORD record: ord-9306a98cc8954d31868dc64429fe6f64
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08227622B2

Reaction notes

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