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

HRID 969458Notes

Reaction equation

HRID 969458 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]>[Ni].C(O)C>[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

4

Reactant 1

HCID 66751245Methyl 3-(2-acetyl-4-benzyloxy-6-nitrophenyl)acrylate

Product 1

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

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

5.0 g (14.07 mmol) methyl 3-(2-acetyl-4-benzyloxy-6-nitro-phenyl)-acrylate are combined with 100 mL ethanol and hydrogenated with Raney nickel as catalyst at 4 bar. The catalyst is separated off and the filtrate is acidified with 15 mL 2 N hydrochloric acid. The product that crystallises out is suction filtered and dried.

Workup

  1. customThe catalyst is separated off
  2. customThe product that crystallises out is suction
  3. filtrationfiltered
  4. customdried

Sources & evidence

ORD record
ord-a9f1ced2c71340fd950e6d46f15755f3
Source dataset
uspto-grants-2007_12
Patent number
US07307076B2

Reaction notes

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