HCID 524499, compound → N-ethyl carbazole

HRID 1911951Notes

Reaction equation

HRID 1911951 reaction equation
[CH2:1]([N:3]1[C:15]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:2]>CC1C=CC=CC=1C>[CH2:1]([N:3]1[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:2].[CH2:1]([N:3]1[C:15]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:2]

Participants

4

Reactant 1

HCID 524499HCID 524499, compound

Product 2

HCID 6836N-ethyl carbazoleYield 82%HCID 524499HCID 524499, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

70 g of 9-ethyl-1,2,3,4-tetrahydrocarbazole was charged along with 3.5 g of filtered wet catalyst obtained from above batch (2 wt % on dry basis) and 35 ml o-xylene. The content were heated under a slow current of nitrogen to achieve 200° C. liquid temperature and maintained for 15 hour to get GC conversion of 82% 9-ethyl carbazole and 17% 9-ethyl-tetrahydrocarbazole. Further, 0.3 g fresh 5%-Pd-carbon (50% moisture) was added at this stage and the reaction was maintained at 200° C. for further 6 hours to get 99% conversion. The reaction mass was then filtered to remove the catalyst and the filtrate was concentrated under reduced pressure to get 67.9 g crude product with GC purity of 98.4%. Filtered catalyst was further recycled three times by adding fresh 5% Pd-c catalyst, 10% of initial catalyst loading to achieve higher conversion.

Workup

  1. temperatureThe content were heated under a slow current of nitrogen
  2. customto achieve 200° C.
  3. temperaturemaintained for 15 hour

Sources & evidence

ORD record
ord-ad6bfffb94194cc385b473ae03886262
Source dataset
uspto-grants-2013_12
Patent number
US08604219B2

Reaction notes

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