3-(4-Methoxy-2-nitrophenyl)acrylic acid methyl ester → 7-Methoxy-3,4-dihydroquinolin-2(1H)-one

HRID 490694Notes

Reaction equation

HRID 490694 reaction equation
C[O:2][C:3](=O)[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][C:7]=1[N+:14]([O-])=O>CO.CCOC(C)=O.CCO.[Pd]>[CH3:13][O:12][C:9]1[CH:8]=[C:7]2[C:6]([CH2:5][CH2:4][C:3](=[O:2])[NH:14]2)=[CH:11][CH:10]=1

Participants

6

Reactant 1

HCID 538271683-(4-Methoxy-2-nitrophenyl)acrylic acid methyl ester

Product 1

HCID 128994187-Methoxy-3,4-dihydroquinolin-2(1H)-oneYield 43.4%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-(4-methoxy-2-nitro-phenyl)-acrylic acid methyl ester (4.00 g, 16.9 mmol) in MeOH (100 mL) and EtOAc (20 mL) is added a slurry of Pd/C (200 mg) in EtOH (20 mL). The suspension is hydrogenated under a pressure of 60 psi for 12 hours. The mixture is then filter through a pad of celite and the filtrate is concentrated and purified on silica gel chromatography column with 30-40-50% EtOAc/Hexanes to obtain the title product (1.30 g, 43%) and an uncyclized by-product (0.60 g).

Workup

  1. filtrationThe mixture is then filter through a pad of celite
  2. concentrationthe filtrate is concentrated
  3. custompurified on silica gel chromatography column with 30-40-50% EtOAc/Hexanes

Sources & evidence

ORD record
ord-ba24b49f2b9643df8e7baaf775c09c06
Source dataset
uspto-grants-2009_05
Patent number
US07528160B2

Reaction notes

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