N-Ethylaniline → 38253-21-3
Reaction equation
Cl[CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=[O:8].[CH2:9]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:10]>>[CH2:9]([N:11]([CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=[O:8])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:10]Participants
3
Reactant 2
Product 1
Procedure
First step is chlorinating cyclohexanone to form 2-chlorocyclohexanone. The obtained 2-chlorocylohexanone is then reacted with N-ethyl aniline to form 2-(N-ethyl anilino)cyclohexanone which is further heated to reflux with simultaneous water removal to complete the cyclization which results in formation of 9-ethyl-tetrahydrocarbazole. Excess of N-ethyl aniline is then removed by treatment with conc. hydrochloric acid and water wash. The obtained organic layer is then washed to make acid free and concentrated to get 9-ethyl tetrahydrocarbazole as a viscous liquid. The crude product is taken for next step without further treatment. N-ethyl aniline is regenerated from aqueous hydrochloride solution by basification.
Sources & evidence
- ORD record
- ord-b1a903bab58a4162a05a6f3fec70a85a
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08604219B2
Reaction notes
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