HCID 12911926, compound → HCID 12911924, compound

HRID 847781Notes

Reaction equation

HRID 847781 reaction equation
[N+:1]([C:4]1[C:16]2[C:17](=[O:23])[C:18]([C:20]([OH:22])=[O:21])=[CH:19][N:14]3[C:15]=2[C:7]([CH:8]2[CH:13]3[CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:6][CH:5]=1)([O-])=O>[OH-].[K+].[Ni]>[NH2:1][C:4]1[C:16]2[C:17](=[O:23])[C:18]([C:20]([OH:22])=[O:21])=[CH:19][N:14]3[C:15]=2[C:7]([CH:8]2[CH:13]3[CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 12911926HCID 12911926, compound

Product 1

HCID 12911924HCID 12911924, compoundYield 68.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 14797Potassium HydroxideSolvent

Procedure

6 g of 3-nitro-7a,8,9,10,11,11a-hexahydro-4-oxo-4H-pyrido[3,2,1-jk]carbazol-5-carboxylic acid was dissolved in 100 ml of a 2% aqueous potassium hydroxide solution and the solution was catalytically reduced by the Parr method (3 kg/cm2) in the presence of 5 g of Raney nickel. After completion of the reduction, the mixture was filtered and the filter cake on the filter paper was washed with water and the combined filtrate and the washing was rendered neutral with glacial acetic acid to precipitate brown crystals. The resulting crystals were filtered, washed with water, dried and recrystallized from DMF-H2O to obtain 3.7 g of 3-amino-7a,8,9,10,11,11a-hexahydro-4-oxo-4H-pyrido[3,2,1-jk]carbazol-5-carboxylic acid having a melting point of 253°-356° C. (with decomposition).

Workup

  1. filtrationAfter completion of the reduction, the mixture was filtered
  2. washthe filter cake on the filter paper was washed with water
  3. customto precipitate brown crystals
  4. filtrationThe resulting crystals were filtered
  5. washwashed with water
  6. customdried
  7. customrecrystallized from DMF-H2O

Sources & evidence

ORD record
ord-856b29937a944f0c8ad50beb02c73db5
Source dataset
uspto-grants-1981_10
Patent number
US04293694

Reaction notes

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