HCID 86694134, compound → 7-Methoxy-1,2-dihydroquinolin-2-one

HRID 707251Notes

Reaction equation

HRID 707251 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11](OCC)=[O:12])=[C:5]([N+:16]([O-])=O)[CH:4]=1>C(O)(=O)C.[Fe]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:6]([CH:9]=[CH:10][C:11](=[O:12])[NH:16]2)=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 86694134HCID 86694134, compound

Product 1

HCID 299427567-Methoxy-1,2-dihydroquinolin-2-oneYield 94%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

(E)-Ethyl 3-(4-methoxy-2-nitrophenyl)acrylate (20.00 g, 80 mmol) and iron powder (3.39 mL, 478 mmol) were mixed in acetic acid (300 mL). The reaction mixture was stirred at room temperature for 4 days. The reaction mixture was filtered through CELITE™. The filtrate was partitioned between ethyl acetate and saturated sodium bicarbonate. The aqueous layer was separated and extracted once more with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, and concentrated. The resulting crude product was diluted with dichloromethane and filtered. The filtrate was diluted with hexanes and partially concentrated. The resulting precipitate was filtered off to yield 7-methoxyquinolin-2(1H)-one (13.16 g, 75 mmol, 94% yield) as a light yellow solid.

Workup

  1. filtrationThe reaction mixture was filtered through CELITE™
  2. customThe filtrate was partitioned between ethyl acetate and saturated sodium bicarbonate
  3. customThe aqueous layer was separated
  4. extractionextracted once more with ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. additionThe resulting crude product was diluted with dichloromethane
  9. filtrationfiltered
  10. additionThe filtrate was diluted with hexanes
  11. concentrationpartially concentrated
  12. filtrationThe resulting precipitate was filtered off

Sources & evidence

ORD record
ord-3d31921fe13c461db02177644189d23f
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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