HCID 23003572, compound → 7-Methoxy-1,2-dihydroquinolin-2-one

HRID 1644281Notes

Reaction equation

HRID 1644281 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1/[CH:10]=[CH:11]/[C:12]([O:14]C)=O>C(#N)C>[CH3:9][O:8][C:6]1[CH:7]=[C:2]2[C:3]([CH:10]=[CH:11][C:12](=[O:14])[NH:1]2)=[CH:4][CH:5]=1

Participants

3

Reactant 1

HCID 23003572HCID 23003572, compound2×

Product 1

HCID 299427567-Methoxy-1,2-dihydroquinolin-2-oneYield 84.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of methyl(2E)-3-(2-amino-4-methoxyphenyl)acrylate (Intermediate 4, 500 mg, 2.4 mmol) in acetonitrile (600 mL) was deoxygenated under vacuum, purged with nitrogen and irradiated at 365 nm with a long wave UV lamp (B-100AP, Blak Ray) for 28 hours. The solvent was removed under reduced pressure and the product was precipitated from dichloromethane (20 mL) by the addition of hexanes (100 mL) to give 357 mg (76% yield) of the crude product as a colorless solid, 90% pure by 1H-NMR (together with 10% dimer), mp 190° C.

Workup

  1. custompurged with nitrogen
  2. customirradiated at 365 nm with a long wave UV lamp (B-100AP, Blak Ray) for 28 hours
  3. customThe solvent was removed under reduced pressure
  4. customthe product was precipitated from dichloromethane (20 mL) by the addition of hexanes (100 mL)

Sources & evidence

ORD record
ord-2af73e31a28b4a2396808dae3ebfb608
Source dataset
uspto-grants-2012_02
Patent number
US08124602B2

Reaction notes

Loading…