HCID 18944263, compound → HCID 18944253, compound

HRID 128752Notes

Reaction equation

HRID 128752 reaction equation
[C:1]1(=[O:27])[N:5]([CH:6]2[CH2:18][C:17]3[C:16]4[C:11](=[CH:12][CH:13]=[C:14]([N+:19]([O-])=O)[CH:15]=4)[NH:10][C:9]=3[CH2:8][CH2:7]2)[C:4](=[O:22])[C:3]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:2]12>C(OCC)(=O)C.[Ni]>[C:4]1(=[O:22])[N:5]([CH:6]2[CH2:18][C:17]3[C:16]4[C:11](=[CH:12][CH:13]=[C:14]([NH2:19])[CH:15]=4)[NH:10][C:9]=3[CH2:8][CH2:7]2)[C:1](=[O:27])[C:2]2=[CH:26][CH:25]=[CH:24][CH:23]=[C:3]12

Participants

4

Reactant 1

HCID 18944263HCID 18944263, compound

Product 1

HCID 18944253HCID 18944253, compoundYield 8.5%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8857Ethyl AcetateSolvent

Procedure

3-phthalimido-6-nitro-1,2,3,4-tetrahydrocarbazole (4.00 g) was dissolved in hot ethyl acetate (130 ml). To the cooled solution was added raney nickel, and the mixture was hydrogenated at an initial pressure of 39 psi at room temperature for 4 hr. After filtering off the insoluble materials, the filtrate was evaporated to dryness, and extracted twice into 20% aqueous methanol and the extracts combined and reduced in volume to give 3-phthalimido-6-amino-1,2,3,4-tetrahydrocarbazole (0.31 g).

Workup

  1. customat room temperature
  2. customfor 4 hr
  3. filtrationAfter filtering off the insoluble materials
  4. customthe filtrate was evaporated to dryness
  5. extractionextracted twice into 20% aqueous methanol

Sources & evidence

ORD record
ord-ca3ea552a12f4e09aee1de2888660c1c
Source dataset
uspto-grants-1995_11
Patent number
US05464864

Reaction notes

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