Hydrochloric Acid → 6-nitro-2,3,4,9-tetrahydro-1H-carbazole
Reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10]N)=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:12]1(=O)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.Cl.O>C(O)(=O)C>[N+:1]([C:4]1[CH:9]=[C:8]2[C:7](=[CH:6][CH:5]=1)[NH:10][C:13]1[CH2:14][CH2:15][CH2:16][CH2:17][C:12]2=1)([O-:3])=[O:2]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
The mixture of p-nitrophenylhydrazine (12) (15.0 g, 97.9 mmol) and cyclohexanone (10.15 ml, 97.9 mmol) in acetic acid (45 ml) was heated and stirred for 20 minutes at 60° C. To the reaction mixture was added conc. hydrochloric acid (15 ml) and the resulting mixture was heated for 1.5 h at reflux. To the reaction mixture was added water (50 ml), heated for 10 minutes at reflux, and allowed to cool to room temperature. The precipitated crystal was filtered off, washed with water, and recrystallized from ethanol-water to give 6-nitrotetrahydrocarbazole (13) (17.0 g; yield 80%).
Workup
- temperaturewas heated
- temperaturethe resulting mixture was heated for 1.5 h
- temperatureat reflux
- temperatureheated for 10 minutes
- temperatureat reflux
- temperatureto cool to room temperature
- filtrationThe precipitated crystal was filtered off
- washwashed with water
- customrecrystallized from ethanol-water
Sources & evidence
- ORD record
- ord-18161e78889a4b9ca3754ffc54eb0cb3
- Source dataset
- uspto-grants-2009_05
- Patent number
- US07534897B2
Reaction notes
Loading…