Dimethylformamide → HCID 21445457, compound

HRID 597565Notes

Reaction equation

HRID 597565 reaction equation
[C:1]([CH2:3][N:4]1[C:12]2[C:13](=[O:23])[N:14]([CH2:21][CH3:22])[C:15]3[C:20]([C:11]=2[C:10]2[CH:9]=[C:8]([Cl:24])[CH:7]=[CH:6][C:5]1=2)=[CH:19][CH:18]=[CH:17][CH:16]=3)#[N:2].CN(C)C=O.O1CCCC1>[Ni].C(O)C>[NH2:2][CH2:1][CH2:3][N:4]1[C:12]2[C:13](=[O:23])[N:14]([CH2:21][CH3:22])[C:15]3[C:20]([C:11]=2[C:10]2[CH:9]=[C:8]([Cl:24])[CH:7]=[CH:6][C:5]1=2)=[CH:19][CH:18]=[CH:17][CH:16]=3

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 21445464HCID 21445464, compound

Product 1

HCID 21445457HCID 21445457, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

5 g. of 7-cyanomethyl-10-chloro-5-ethyl-7H-indolo[2,3-c]-quinolin-6(5H)-one was dissolved in 200 ml. of boiling dimethylformamide. After cooling, 200 ml. of tetrahydrofuran, 100 ml. of ethanol and Raney nickel were added. The mixture was hydrogenated for 21/2 hours at atmospheric pressure. The catalyst was separated by filtration and the filtrate was evaporated. Crystallization of the residue from ethanol yielded 2.9 g. (57 percent) of 7-(2-aminoethyl)-10-chloro-5-ethyl-7H-indolo[2,3-c]quinolin-6(5H)-one, which after recrystallization from ethanol had a melting point of 166°-169°.

Workup

  1. temperatureAfter cooling
  2. custom2 hours
  3. customThe catalyst was separated by filtration
  4. customthe filtrate was evaporated
  5. customCrystallization of the residue from ethanol
  6. customyielded 2.9 g
  7. custom(57 percent) of 7-(2-aminoethyl)-10-chloro-5-ethyl-7H-indolo[2,3-c]quinolin-6(5H)-one, which after recrystallization from ethanol

Sources & evidence

ORD record
ord-c63854492d754f51a269508b4d84ba30
Source dataset
uspto-grants-1977_03
Patent number
US04014883

Reaction notes

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