Dimethylformamide → 9H-carbazol-9-amine

HRID 2051200Notes

Reaction equation

HRID 2051200 reaction equation
C[N:2](C)C=O.[CH:6]1[C:18]2[NH:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]=2[CH:9]=[CH:8][CH:7]=1.[OH-].[K+].NOS(O)(=O)=O>O>[CH:15]1[C:16]2[N:17]([NH2:2])[C:18]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[C:11]=2[CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6854CarbazoleHCID 14797Potassium HydroxideHCID 76284hydroxylamine-O-sulfonic acid

Product 1

HCID 2762079H-carbazol-9-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into 250 ml of dimethylformamide was dissolved 25 g of carbazole. This solution was cooled with an ice-salt bath and 42 g of potassium hydroxide was added portionwise. To this mixture was added hydroxylamine-O-sulfonic acid. After two hours the mixture was stirred with water and extracted with ethyl acetate. The organic extracts were washed with water and brine. After filtering the solvent was evaporated and the residue was eluted with 25% dichloromethane in hexane on a silica column to yield 9.5 g of a mixture of carbazole and 9H-carbazol-9-amine.

Workup

  1. temperatureThis solution was cooled with an ice-salt bath
  2. extractionextracted with ethyl acetate
  3. washThe organic extracts were washed with water and brine
  4. filtrationAfter filtering the solvent
  5. customwas evaporated
  6. washthe residue was eluted with 25% dichloromethane in hexane on a silica column

Sources & evidence

ORD record
ord-5d62ab80ad564fa2a32f6ce73e22f750
Source dataset
uspto-grants-1991_05
Patent number
US05017578

Reaction notes

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