Cyclohexanone → 3-Methoxy-9H-carbazole

HRID 1763221Notes

Reaction equation

HRID 1763221 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10]N)=[CH:6][CH:5]=1.[C:12]1(=O)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1>[Pd].C1(C)C(C)=CC=CC=1>[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]2[NH:10][C:12]3[C:17]([C:6]=2[CH:5]=1)=[CH:16][CH:15]=[CH:14][CH:13]=3

Participants

5

Reactant 2

HCID 7967CyclohexanoneHCID 27239044-Methoxyphenylhydrazine hydrochloride

Product 1

HCID 5196213-Methoxy-9H-carbazoleYield 74%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 7237O-XyleneSolvent

Procedure

Bis-1,3(N-3'-methoxycarbazolyl)propane. Reaction of p-methoxyphenylhydrazine hydrochloride with cyclohexanone (exothermic) was carried out as for the methyl substituted compound (See Liebigs Ann. der Chemie, 359, 52, 1908) in 82% yield, mp 105°-7.5° C. This compound was dehydrogenated with 10% palladium on charcoal in xylene, as above, to give 74% of 3-methoxycarbazole, recrystallized from benzene/heptane, mp 148.5°-9.5° C (lit. mp 150.5°-1.0° C).

Sources & evidence

ORD record
ord-84dae3a0ad67415c81801ff311543c61
Source dataset
uspto-grants-1978_09
Patent number
US04111850

Reaction notes

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