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

HRID 255159Notes

Reaction equation

HRID 255159 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-1-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-8528ac3d6bb241b09bab9c9ea53cb3b7
Source dataset
uspto-grants-2011_01
Patent number
US07875715B2

Reaction notes

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