N-(t-butylphenyl) carbazolone → N-(t-butylphenyl)hydroxycarbazole

HRID 1488324Notes

Reaction equation

HRID 1488324 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[C:23]2[C:22](=[O:24])[CH2:21][CH:20]=[CH:19][C:18]=2[C:17]2[C:12]1=[CH:13][CH:14]=[CH:15][CH:16]=2)([CH3:4])([CH3:3])[CH3:2]>[Pd].C1(OC2C=CC=CC=2)C=CC=CC=1>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[C:23]2[C:22]([OH:24])=[CH:21][CH:20]=[CH:19][C:18]=2[C:17]2[C:12]1=[CH:13][CH:14]=[CH:15][CH:16]=2)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 86688393N-(t-butylphenyl) carbazolone2×

Product 1

HCID 86688394N-(t-butylphenyl)hydroxycarbazoleYield 84.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 7583Diphenyl EtherSolvent

Procedure

In a 500 ml two-neck flask, N-(t-butylphenyl) carbazolone (Compound F, 13 g) and diphenylether (100 ml) were mixed, and the 10% Pd/C (13 g) was added thereto. This reaction solution was refluxed and stirred for 30 minutes to 1 hour. When the reaction was completed, 80% of diphenylether was removed by distillation under reduced pressure, and a catalyst was removed using celite. The filtrate was washed again with ethylacetate. The filtrate was concentrated under reduced pressure and separated using a column chromatography, thereby obtaining 11 g of N-(t-butylphenyl)hydroxycarbazole (Compound G).

Workup

  1. temperatureThis reaction solution was refluxed
  2. custom80% of diphenylether was removed by distillation under reduced pressure
  3. customa catalyst was removed
  4. washThe filtrate was washed again with ethylacetate
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customseparated

Sources & evidence

ORD record
ord-48b6ac7dcb684829b888eb9a98d5ae86
Source dataset
uspto-grants-2016_08
Patent number
US09431616B2

Reaction notes

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