8-Methoxy-6-nitro-3,4-dihydroquinolin-2(1H)-one → 6-Amino-8-methoxy-3,4-dihydrocarbostyril

HRID 1649002Notes

Reaction equation

HRID 1649002 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([O:14][CH3:15])[CH:13]=1)[NH:10][C:9](=[O:16])[CH2:8][CH2:7]2)([O-])=O.[H][H]>C(O)C.[C].[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([O:14][CH3:15])[CH:13]=1)[NH:10][C:9](=[O:16])[CH2:8][CH2:7]2

Participants

5

Reactant 2

HCID 130510718-Methoxy-6-nitro-3,4-dihydroquinolin-2(1H)-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 130510706-Amino-8-methoxy-3,4-dihydrocarbostyrilYield 98.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

6-Nitro-8-methoxy-3,4-dihydrocarbostyril (2 g) and 5% palladium-carbon (0.2 g) were added in ethanol (50 ml) and catalytic reduction was conducted at a hydrogen gas pressure of 3 kg/cm2 for 1 hour. Then, the reaction mixture was filtered and the filtrate was concentrated. The residue was recrystallized from benzene to give 1.7 g of 6-amino-8-methoxy-3,4-dihydrocarbostyril.

Workup

  1. filtrationThen, the reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe residue was recrystallized from benzene

Sources & evidence

ORD record
ord-3ea3c1d9c82b40eba481b1683f89d792
Source dataset
uspto-grants-1983_11
Patent number
US04414390

Reaction notes

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