4-Bromophenylhydrazine hydrochloride → N-(6-bromo-1,3,4,9-tetrahydro-2H-carbazol-2-yl)acetamide

HRID 66784

Reaction equation

HRID 66784 reaction equation
O=[C:2]1[CH2:7][CH2:6][CH2:5][CH:4]([NH:8][C:9](=[O:11])[CH3:10])[CH2:3]1.Cl.[Br:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20]N)=[CH:16][CH:15]=1>CC(O)=O>[Br:13][C:14]1[CH:15]=[C:16]2[C:17](=[CH:18][CH:19]=1)[NH:20][C:2]1[CH2:3][CH:4]([NH:8][C:9](=[O:11])[CH3:10])[CH2:5][CH2:6][C:7]2=1

Participants

4

Reactant 2

HCID 121574-Bromophenylhydrazine hydrochlorideHCID 20529251N-(3-oxocyclohexyl)acetamide

Product 1

HCID 20529232N-(6-bromo-1,3,4,9-tetrahydro-2H-carbazol-2-yl)acetamide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
80 °C

Procedure

A solution of 0.05 mol of N-(3-oxocyclohexyl)acetamide in 100 ml of glacial HOAc was stirred and heated at 80° C. while adding during 15-30 minutes a warm solution of 0.05 mol of 4-bromophenylhydrazine hydrochloride in 300 ml of glacial HOAc. After an additional 3 hr at 85°, most of the HOAc was evaporated. The residue was triturated with H2O, until solid, the resulting solid was filtered, and recrystallized from ethanol to give the title compound, mp 210°-211°.

Workup

  1. custommost of the HOAc was evaporated
  2. customThe residue was triturated with H2O, until solid
  3. filtrationthe resulting solid was filtered
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-2bfa85bc87604b8b955eec3ed01d9979
Source dataset
uspto-grants-1982_08
Patent number
US04343812

Linked notes

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