Methyl 3-(2-acetyl-4-benzyloxy-6-nitrophenyl)acrylate → 5-acetyl-7-benzyloxy-3,4-dihydro-1H-quinolin-2-one

HRID 1372905Notes

Reaction equation

HRID 1372905 reaction equation
[C:1]([C:4]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:7]=[C:6]([N+:18]([O-])=O)[C:5]=1[CH:21]=[CH:22][C:23]([O:25]C)=O)(=[O:3])[CH3:2].[H][H]>C(O)C.[Ni]>[C:1]([C:4]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:7]=[C:6]2[C:5]=1[CH2:21][CH2:22][C:23](=[O:25])[NH:18]2)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 66751245Methyl 3-(2-acetyl-4-benzyloxy-6-nitrophenyl)acrylateHCID 178418361HCID 178418361, compound

Product 1

HCID 210728505-acetyl-7-benzyloxy-3,4-dihydro-1H-quinolin-2-one

Reagents, catalysts & solvents 2

HCID 935NickelCatalyst2×HCID 702EthanolSolvent

Procedure

A suspension of methyl 3-(2-acetyl-4-benzyloxy-6-nitrophenyl)-acrylate (5.0 g, 14.07 mmol) in ethanol (100 mL) is hydrogenated with Raney nickel (3 g) at ambient temperature and 4 bar hydrogen pressure. After 6 hours more Raney nickel (2 g) is added and the mixture is hydrogenated for a further 2 hours. The catalyst is separated off and the filtrate is combined with 2 M aqueous hydrochloric acid (15 mL). The product that crystallises out is filtered off and dried.

Workup

  1. customThe catalyst is separated off
  2. customThe product that crystallises out
  3. filtrationis filtered off
  4. customdried

Sources & evidence

ORD record
ord-9db71bca35e541709c0fc0d7d91ebe27
Source dataset
uspto-grants-2007_01
Patent number
US07160882B2

Reaction notes

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