Cyclohexanone → 6-Bromo-1,2,3,4-tetrahydrocarbazole

HRID 731040Notes

Reaction equation

HRID 731040 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)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1>C(O)C>[Br:2][C:3]1[CH:8]=[C:7]2[C:6](=[CH:5][CH:4]=1)[NH:9][C:12]1[CH2:13][CH2:14][CH2:15][CH2:16][C:11]2=1

Participants

4

Reactant 2

HCID 7967CyclohexanoneHCID 121574-Bromophenylhydrazine hydrochloride

Product 1

HCID 2688776-Bromo-1,2,3,4-tetrahydrocarbazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The desired product was prepared using a procedure similar to step 1 of example 3. Thus, 4-bromophenylhydrazine, hydrochloride (5.398 g, 24.15 mmol) was reacted with cyclohexanone (2.257 g, 23 mmol) in ethanol (60 ml) to give the product (4.871 g, 19.473 mmol, 85%) as a white solid, mp 148-151° C. 1H NMR (DMSO-d6) δ 1.74-1.83 (m, 4H), 2.57 (t, J=6.0 Hz, 2H), 2.68 (t, J=5.7 Hz, 2H), 7.06 (dd, J=1.8, 8.4 Hz, 1H), 7.18 (d, J=8.4 Hz, 1H), 7.46 (s, 1H), 10.84 (s, 1H); [ESI(−)], m/z 248/250 (M−H)−.

Sources & evidence

ORD record
ord-31748c63fcc44796a9c802f746a7bf58
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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