Hydrazine hydrate (1:1) → 4-Methyl-3-(2'-oxospiro[cyclopentane-1,3'-indoline]-6'-yl)benzohydrazide

HRID 1619143Notes

Reaction equation

O.[NH2:2][NH2:3].[CH3:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11]C)=O)=[CH:7][C:6]=1[C:15]1[CH:23]=[C:22]2[C:18]([C:19]3([CH2:28][CH2:27][CH2:26][CH2:25]3)[C:20](=[O:24])[NH:21]2)=[CH:17][CH:16]=1>C(O)C>[CH3:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([NH:2][NH2:3])=[O:11])=[CH:7][C:6]=1[C:15]1[CH:23]=[C:22]2[C:18]([C:19]3([CH2:28][CH2:27][CH2:26][CH2:25]3)[C:20](=[O:24])[NH:21]2)=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Hydrazine monohydrate (0.67 mL, 13.8 mmol) was added to a stirred solution of methyl 4-methyl-3-(2′-oxospiro[cyclopentane-1,3′-indoline]-6′-yl)benzoate (preparation 53a, 0.46 g, 1.3 mmol) in ethanol (6 mL) and the mixture was stirred at 80° C. After 3 days, the mixture was cooled and concentrated in vacuo. The crude material was purified by flash chromatography (50:1 dichloromethane/methanol) to give the title compound (0.16 g, 19%) as a solid.

Workup

temperaturethe mixture was cooled
concentrationconcentrated in vacuo
customThe crude material was purified by flash chromatography (50:1 dichloromethane/methanol)

Sources & evidence

ORD record: ord-7faf948398374d0b86a4b2b1ec9dccd5
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772288B2

Reaction notes

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