Water → 6-Bromo-1,2,3,9-tetrahydro-4H-carbazol-4-one

HRID 4377Notes

Reaction equation

HRID 4377 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8]N=C2CCCC(=O)C2)=[CH:4][CH:3]=1.[OH2:17]>C(O)(=O)C.[Cl-].[Zn+2].[Cl-]>[Br:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][CH:7]=1)[NH:8][C:3]1[CH2:4][CH2:5][CH2:6][C:7](=[O:17])[C:2]2=1

Participants

5

Reactant 2

HCID 962WaterHCID 566239871,3-Cyclohexanedione mono(4-bromophenylhydrazone)

Product 1

HCID 201524426-Bromo-1,2,3,9-tetrahydro-4H-carbazol-4-one

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 176Acetic AcidSolvent

Procedure

The product of Stage (i) (1.5 g) was heated under reflux with dry zinc chloride (16 g) in glacial acetic acid (75 ml) for 24 h. The mixture was cooled, poured into water (200 ml), and the resulting solid filtered off and dried (0.95 g). Purification by flash chromatography (E) gave the title compound as a solid (125 mg). T.l.c. (F), Rf 0.65

Workup

  1. temperatureThe mixture was cooled
  2. filtrationthe resulting solid filtered off
  3. customdried (0.95 g)
  4. customPurification by flash chromatography (E)

Sources & evidence

ORD record
ord-477e144581644ea4bec3777f5ed06716
Source dataset
uspto-grants-1988_02
Patent number
US04725615

Reaction notes

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