Ethanol → HCID 16084834, compound

HRID 1586593Notes

Reaction equation

HRID 1586593 reaction equation
[C:1]([CH2:3][CH2:4][N:5]1[C:17]2[C:16]3[N:18]([CH3:25])[C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=4[C:15]=3[C:14]3[C:26](=[O:30])[NH:27][C:28](=[O:29])[C:13]=3[C:12]=2[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)#[N:2].C(O)C>CO.[Ni]>[NH2:2][CH2:1][CH2:3][CH2:4][N:5]1[C:17]2[C:16]3[N:18]([CH3:25])[C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=4[C:15]=3[C:14]3[C:26](=[O:30])[NH:27][C:28](=[O:29])[C:13]=3[C:12]=2[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2

Participants

5

Reactant 2

HCID 702EthanolHCID 5327858HCID 5327858, compound

Product 1

HCID 16084834HCID 16084834, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

760 mg (1.94 mmol) 12-(2-Cyanoethyl)-6,7,12,13-tetrahydro-13-methyl-5,7-dioxo-5H-indolo[2,3-a]-pyrrolo[3,4-c]carbazole (Example 1a) in 100 ml methanol are hydrogenated in the presence of 500 mg Raney nickel at 60° C. and 50-65 bar pressure for 20 hours in an autoclave. The reaction mixture is evaporated, the residue is taken up in 100 ml dimethylformamide, filtered off from the catalyst and again evaporated in a vacuum. The residue is chromatographed on silica gel with dichloromethane/methanol saturated with ammonia (95:5 v/v). The fraction with the Rf of 0.1 is isolated, stirred with ethanol and the undissolved product is filtered off. 12-(3-aminopropyl)-6,7,12,13-tetrahydro-13-methyl-5,7-dioxo-5H-indolo[2,3-a]pyrrolo[3,4-c]-carbazole is obtained as an amorphous yellow powder which decomposes from about 250° C.

Workup

  1. customThe reaction mixture is evaporated
  2. filtrationfiltered off from the catalyst
  3. customagain evaporated in a vacuum
  4. customThe residue is chromatographed on silica gel with dichloromethane/methanol saturated with ammonia (95:5 v/v)
  5. customThe fraction with the Rf of 0.1 is isolated
  6. filtrationthe undissolved product is filtered off

Sources & evidence

ORD record
ord-552e837f6d56429491bd991c30ae2abc
Source dataset
uspto-grants-1999_08
Patent number
US05945440

Reaction notes

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