4-Bromophenylhydrazine hydrochloride → 3-Phthalimido-6-bromo-1,2,3,4-tetrahydrocarbazole

HRID 128751Notes

Reaction equation

HRID 128751 reaction equation
Cl.[Br:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9]N)=[CH:5][CH:4]=1.[C:11]1(=[O:28])[N:15]([CH:16]2[CH2:21][CH2:20][C:19](=O)[CH2:18][CH2:17]2)[C:14](=[O:23])[C:13]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:12]12>C(O)CCC>[C:14]1(=[O:23])[N:15]([CH:16]2[CH2:17][C:18]3[C:7]4[C:6](=[CH:5][CH:4]=[C:3]([Br:2])[CH:8]=4)[NH:9][C:19]=3[CH2:20][CH2:21]2)[C:11](=[O:28])[C:12]2=[CH:27][CH:26]=[CH:25][CH:24]=[C:13]12

Participants

4

Reactant 2

HCID 121574-Bromophenylhydrazine hydrochlorideHCID 119983912-(4-oxocyclohexyl)-2,3-dihydro-1H-isoindole-1,3-dione

Product 1

HCID 189442543-Phthalimido-6-bromo-1,2,3,4-tetrahydrocarbazoleYield 104.1%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

Reaction of 4-bromophenylhydrazine hydrochloride (4.0 g, 18.1 mmol) with 4-phthalimido-cyclohexanone (4.39 g, 18.1 mmol) in refluxing n-butanol for 20 min, followed by cooling, filtration, and evaporation of the filtrate to dryness yielded 3-phthalimido-6-bromo-1,2,3,4-tetrahydrocarbazole as an orange solid (7.45 g).

Workup

  1. temperatureby cooling
  2. filtrationfiltration, and evaporation of the filtrate to dryness

Sources & evidence

ORD record
ord-356706dc8cf34c75a7037dfde7dad757
Source dataset
uspto-grants-1995_11
Patent number
US05464864

Reaction notes

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