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

HRID 33380Notes

Reaction equation

HRID 33380 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 at 4 bar with Raney nickel as catalyst. 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-16e22edf921249b6a22ad11e337a543d
Source dataset
uspto-grants-2008_09
Patent number
US07429583B2

Reaction notes

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