Sodium Hydroxide → 4-Hydroxycarbazole

HRID 646647

Reaction equation

HRID 646647 reaction equation
[CH2:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[C:4](=[O:14])[CH2:3][CH2:2]1.[OH-].[Na+]>[Ni].O>[OH:14][C:4]1[C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[NH:12][C:13]=2[CH:1]=[CH:2][CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 9291301,2,3,9-Tetrahydro-4H-carbazol-4-one

Product 1

HCID 1042514-Hydroxycarbazole

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 962WaterSolvent

Procedure

To a reactor containing water (1 L) was added Raney nickel (35 g) followed by 1,2,3,9-tetrahydrocarbazole-4-one (50 g) and sodium hydroxide (15 g). The contents were heated to reflux and maintained for about 20 hours. The catalyst was filtered off and the filtrate was acidified to obtain a solid, which was filtered and dried to obtain the title compound. When necessary, the title compound was further purified by dissolving in 10% sodium hydroxide solution, treating with activated charcoal and precipitation from dilute hydrochloric acid to give off-white to grey crystals of 4-hydroxy carbazole in 50% yield.

Workup

  1. temperatureThe contents were heated
  2. temperatureto reflux
  3. temperaturemaintained for about 20 hours
  4. filtrationThe catalyst was filtered off
  5. customto obtain a solid, which
  6. filtrationwas filtered
  7. customdried

Sources & evidence

ORD record
ord-8478a4ba9d0a4efe8b2edf31f4d6d925
Source dataset
uspto-grants-2010_04
Patent number
US07705163B2

Linked notes

Loading…