Ethyl Acetate → 3,6-Dimethylcarbazole

HRID 1763220Notes

Reaction equation

HRID 1763220 reaction equation
[CH3:1][CH:2]1[CH2:14][C:13]2[C:12]3[C:7](=[CH:8][CH:9]=[C:10]([CH3:15])[CH:11]=3)[NH:6][C:5]=2[CH2:4][CH2:3]1.C(OCC)(=O)C>[Pd].C1(C)C(C)=CC=CC=1>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:6][C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][C:10]([CH3:15])=[CH:9][CH:8]=3

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 2786371HCID 2786371, compound

Product 1

HCID 6069653,6-DimethylcarbazoleYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 7237O-XyleneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 12.0 g (60.3 mmol) of 3,6-dimethyl-1,2,3,4,-tetrahydrocarbazole and 3.6 g of 10% palladium on charcoal (46-190, Strem Chemicals, Danvers, Mass.) in 120 ml xylene was refluxed vigorously (150° C) overnight. Addition of 200 ml of ethyl acetate, filtration of the cooled mixture through Celite 545 and evaporation of solvents gave 11.0 g (94%) of 3,6-dimethylcarbazole, mp 218°-21° C (lit. mp 217°-18° C).

Workup

  1. customthrough Celite 545 and evaporation of solvents

Sources & evidence

ORD record
ord-f52b1961605247dba97c6939be799a49
Source dataset
uspto-grants-1978_09
Patent number
US04111850

Reaction notes

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