HCID 53779524, compound → HCID 54476443, compound

HRID 436507Notes

Reaction equation

HRID 436507 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:18][CH2:17][C:16]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([N+:19]([O-])=O)[CH:14]=3)[NH:9][C:8]=2[CH2:7]1)=[O:5])[CH3:2].[H][H]>[Ni].C(O)C>[CH2:1]([O:3][C:4]([CH:6]1[CH2:18][CH2:17][C:16]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([NH2:19])[CH:14]=3)[NH:9][C:8]=2[CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 53779524HCID 53779524, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 54476443HCID 54476443, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1.3 g. of 6-nitro-1,2,3,4-tetrahydrocarbazole-2-carboxylic acid ethyl ester, 0.5 teaspoonful of Raney nickel and 100 ml. of ethanol was shaken in a Parr hydrogenation apparatus under 3.7 atmospheres of hydrogen at room temperature. After 2 hours of shaking the uptake of hydrogen had stopped. The catalyst was removed by filtration and the filtrate was concentrated to dryness, yielding 1.2 g. of product. Following recrystallization from a mixture of hexane and ethyl acetate, a yield of 0.8 g. of 6-amino-1,2,3,4-tetrahydrocarbazole-2-carboxylic acid ethyl ester, m.p. 123°-124° was obtained.

Workup

  1. additionA mixture of 1.3 g
  2. customThe catalyst was removed by filtration
  3. concentrationthe filtrate was concentrated to dryness
  4. customyielding 1.2 g
  5. customrecrystallization
  6. additionfrom a mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-f8cbc6642296422e9db167fbdc9282d4
Source dataset
uspto-grants-1977_02
Patent number
US04009181

Reaction notes

Loading…