Ethanol → 4-Bromo-N-(1,3-dioxohexahydro-1H-isoindol-2(3H)-yl)benzamide

HRID 41095

Reaction equation

HRID 41095 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][NH2:9])=[O:7])=[CH:4][CH:3]=1.[CH2:12]([OH:14])[CH3:13]>>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][N:9]2[C:12](=[O:14])[CH:13]3[CH:5]([CH2:4][CH2:3][CH2:2][CH2:11]3)[C:6]2=[O:7])=[O:7])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 702EthanolHCID 222194-Bromobenzohydrazide

Product 1

HCID 114280804-Bromo-N-(1,3-dioxohexahydro-1H-isoindol-2(3H)-yl)benzamideYield 52%

Procedure

A mixture of cis-cyclohexanedicarboxylic anhydride (150 mg, 0.97 mmol) and 4-bromobenzoic hydrazide (220 mg, 1.02 mmol) in ethanol (10 mL) was heated under argon overnight. The solvent was removed via rotary evaporation. Purification by column chromatography on silica gel using 1/1 hexane/ethyl acetate as eluent provided 179 mg (52%) of the desired product as a white solid.

Workup

  1. temperaturewas heated under argon overnight
  2. customThe solvent was removed via rotary evaporation
  3. customPurification by column chromatography on silica gel using 1/1 hexane/ethyl acetate as eluent

Sources & evidence

ORD record
ord-c707887e33bb4aedbeba13319ebd4216
Source dataset
uspto-grants-2013_09
Patent number
US08530509B2

Linked notes

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