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

HRID 2223115Notes

Reaction equation

HRID 2223115 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 crystallizes out is filtered off and dried. Yield: 1.0 g (24%); mass spectroscopy: [M+H]+=296.

Workup

  1. waitthe mixture is hydrogenated for a further 2 hours
  2. customThe catalyst is separated off
  3. customThe product that crystallizes out
  4. filtrationis filtered off
  5. customdried

Sources & evidence

ORD record
ord-3483f51b9592401f8489ae476c428e7d
Source dataset
uspto-grants-2008_05
Patent number
US07375104B2

Reaction notes

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