Reaction #61658

ord-16e22edf921249b6a22ad11e337a543d

Reaction equation

COC(=O)C=Cc1c(C(C)=O)cc(OCc2ccccc2)cc1[N+](=O)[O-]
methyl 3-(2-acetyl-4-benzyloxy-6-nitro-phenyl)-acrylate
→
CC(=O)c1cc(OCc2ccccc2)cc2c1CCC(=O)N2
5-acetyl-7-benzyloxy-3,4-dihydro-1H-quinolin-2-one

Reactants

COC(=O)C=Cc1c(C(C)=O)cc(OCc2ccccc2)cc1[N+](=O)[O-]
methyl 3-(2-acetyl-4-benzyloxy-6-nitro-phenyl)-acrylate

Reagents

[Ni]
Raney nickel

Solvents

CCO
ethanol

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherThe catalyst is separated off
  2. 2
    OtherThe product that crystallises out is suction
  3. 3
    Filtrationfiltered
  4. 4
    Otherdried

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07429583B2uspto-grants-2008_09