HCID 14423248, compound → HCID 14423299, compound

HRID 1193755Notes

Reaction equation

HRID 1193755 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[C:17]3[N:16]=[CH:15][CH:14]=[CH:13][C:12]=3[C:11](=[O:18])[C:10]3[S:19][CH2:20][CH2:21][C:9]2=3)[CH:5]=[CH:6][CH:7]=1>[Ni].C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[C:17]3[N:16]=[CH:15][CH:14]=[CH:13][C:12]=3[C:11](=[O:18])[C:10]3[S:19][CH:20]=[CH:21][C:9]2=3)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 14423248HCID 14423248, compound

Product 1

HCID 14423299HCID 14423299, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

Reflux a mixture of 4-(3-chlorophenyl)-2,3-dihydrothieno[3,2-b][1,8]naphthyridin-9(9H)-one (0.11 g), ethanol (100 ml), and commercial aged Raney nickel (from 5 ml of an aqueous suspension) for 10 hours under nitrogen. Filter the resulting mixture, evaporate the solvent, and chromatograph the residue over silica gel. Elute with CHCl3 to give 4-(3-chlorophenyl)-thieno[3,2-b][1,8]naphthyridin-9(4H)-one, m.p. 264°-267° C. from CHCl3 hexane.

Workup

  1. temperatureReflux
  2. filtrationFilter the resulting mixture
  3. customevaporate the solvent, and chromatograph the residue over silica gel
  4. washElute with CHCl3

Sources & evidence

ORD record
ord-a3d35643ec214ba2a86b0b858a29b738
Source dataset
uspto-grants-1989_03
Patent number
US04810708

Reaction notes

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