HCID 13236317, compound → HCID 13236319, compound

HRID 1649217Notes

Reaction equation

HRID 1649217 reaction equation
[N+:1]([C:4]1[CH:28]=[CH:27][C:7]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([C:16]3[CH:17]=[C:18]4[C:23](=[CH:24][CH:25]=3)[NH:22][C:21](=[O:26])[CH2:20][CH2:19]4)[CH2:12][CH2:11]2)=[O:9])=[CH:6][CH:5]=1)([O-])=O>[C].[Pd].CO>[NH2:1][C:4]1[CH:28]=[CH:27][C:7]([C:8]([N:10]2[CH2:11][CH2:12][N:13]([C:16]3[CH:17]=[C:18]4[C:23](=[CH:24][CH:25]=3)[NH:22][C:21](=[O:26])[CH2:20][CH2:19]4)[CH2:14][CH2:15]2)=[O:9])=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 13236317HCID 13236317, compound

Product 1

HCID 13236319HCID 13236319, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

6-[4-(4-Nitrobenzoyl)-1-piperazinyl]-3,4-dihydrocarbostyril (400 mg) was added to 20 ml of methanol and reduced at room temperature at atmospheric pressure using 50 mg of 10% palladium-carbon as a catalyst. After completion of absorption of hydrogen gas the catalyst was removed by filtration. The filtrate was subjected to distillation under reduced pressure and the residue was purified through silica gel column chromatography. Recrystallization from ethanol gave 210 mg of 6-[4-(4-aminobenzoyl)-1-piperazinyl]-3,4-dihydrocarbostyril, m.p. 244°-246° C., pale yellow needles.

Workup

  1. customreduced at room temperature at atmospheric pressure
  2. customAfter completion of absorption of hydrogen gas the catalyst
  3. customwas removed by filtration
  4. distillationThe filtrate was subjected to distillation under reduced pressure
  5. customthe residue was purified through silica gel column chromatography
  6. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-3e68180ff4464aaa86dedbecef1e3e01
Source dataset
uspto-grants-1983_11
Patent number
US04415572

Reaction notes

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