2,3-Dihydro-1-methyl-4(1H)-quinolinone → HCID 87105755, compound

HRID 1803767Notes

Reaction equation

HRID 1803767 reaction equation
Cl.[O:2]([NH2:4])[CH3:3].[CH3:5][N:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=O)[CH2:8][CH2:7]1>N1C=CC=CC=1>[CH3:3][O:2][N:4]=[C:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:6]([CH3:5])[CH2:7][CH2:8]1

Participants

4

Reactant 2

HCID 4204192,3-Dihydro-1-methyl-4(1H)-quinolinoneHCID 521874O-Methylhydroxylamine hydrochloride

Product 1

HCID 87105755HCID 87105755, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methoxylamine hydrochloride (0.88 g, 10.6 mmol) was added to a solution of Example 17A (1.55 g, 9.6 mmol) in pyridine (20 mL) and the mixture stirred overnight at ambient temperature. The mixture was concentrated under reduced pressure and ethyl acetate (200 mL) was added. The organic layer was washed twice with water (200 mL) and brine, dried over sodium sulfate, filtered, and concentrate under reduced pressure. The residue was chromatographed on silica gel eluting with 0-20% ethyl acetate in hexane to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 2.76 (t, J=6.61 Hz, 2H), 2.83 (s, 3H), 3.11 (t, J=6.61 Hz, 2H), 3.87 (s, 3H), 6.69 (t, J=7.46 Hz, 1H), 6.75 (d, J=8.48 Hz, 1H), 7.22 (td, J=7.80, 1.70 Hz, 1H), 7.73 (dd, J=7.80, 1.70 Hz, 1H). MS (DCI) m/z 191.07 (M+H)1.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure and ethyl acetate (200 mL)
  2. additionwas added
  3. washThe organic layer was washed twice with water (200 mL) and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrate under reduced pressure
  7. customThe residue was chromatographed on silica gel eluting with 0-20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-e9ce108ee4794726bc80d492d537cb21
Source dataset
uspto-grants-2013_01
Patent number
US08350083B2

Reaction notes

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