Dimethylformamide → 5,7,8,9,10,11-Hexahydrocyclopent[a]pyrrolo[3,4-c]carbazole-5(6H)-one

HRID 1020902Notes

Reaction equation

HRID 1020902 reaction equation
[C:1]([C:3]1[C:15]([C:16](OCC)=O)=[C:14]2[C:6]([NH:7][C:8]3[C:13]2=[CH:12][CH:11]=[CH:10][CH:9]=3)=[C:5]2[CH2:21][CH2:22][CH2:23][C:4]=12)#[N:2].CN(C=[O:28])C>[Ni]>[CH:16]1[C:15]2[C:3]([C:4]3[C:5]([CH2:21][C:22](=[O:28])[CH:23]=3)=[C:6]3[C:14]=2[C:13]2[CH2:12][CH2:11][CH2:10][CH2:9][C:8]=2[NH:7]3)=[CH:1][N:2]=1

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 21923197Ethyl 4-cyano-1,2,3,10-tetrahydrocyclopenta[a]carbazole-5-carboxylate

Product 1

HCID 219232385,7,8,9,10,11-Hexahydrocyclopent[a]pyrrolo[3,4-c]carbazole-5(6H)-oneYield 100%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

Ethyl 4-Cyano-1,2,3,10-tetrahydrocyclopenta[a]carbazole-5-carboxylate (14 mg) in DMF (1.6 mL) was hydrogenated at 55 psi over W2 Raney nickel (150 mg) for 2.5 days. The catalyst was removed by filtration and the DMF was evaporated in vacuo to give the product (12 mg, 100% yield) as light brown crystals. A sample was recrystallized from DMF, boiled with ethanol, cooled, and filtered to give the product as an off-white solid, mp>300° C. NMR (DMSO-d6) δ 11.45 (s, 1H), 9.06 (d, 1H), 8.47 (s, 1H), 7.51 (d, 1H), 7.40 (t, 1H), 7.16 (t, 1H), 4.41 (s, 2H), 3.21 (t, 2H), 3.04 (t, 2H), 2.30 (quintet, 2H). Anal. Calcd for C17H14N2O: C, 77.84; H, 5.38; N, 10.68. Found: C, 77.40; H, 5.66; N, 10.49.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe DMF was evaporated in vacuo

Sources & evidence

ORD record
ord-f54aacd5eef8408eb24f007559737d3a
Source dataset
uspto-grants-2014_05
Patent number
US08716493B2

Reaction notes

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