O-Methylhydroxylamine hydrochloride → HCID 136359357, compound

HRID 1803765Notes

Reaction equation

HRID 1803765 reaction equation
Cl.[O:2]([NH2:4])[CH3:3].[F:5][C:6]([F:19])([F:18])[C:7]1[CH:16]=[C:15]2[C:10]([C:11](=O)[CH2:12][CH2:13][NH:14]2)=[CH:9][CH:8]=1>N1C=CC=CC=1>[CH3:3][O:2][N:4]=[C:11]1[C:10]2[C:15](=[CH:16][C:7]([C:6]([F:19])([F:5])[F:18])=[CH:8][CH:9]=2)[NH:14][CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 14501412HCID 14501412, compound

Product 1

HCID 136359357HCID 136359357, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methoxylamine hydrochloride (4.14 g, 49.5 mmol) was added to a solution of Example 16C (9.69 g, 45.0 mmol) in pyridine (40 mL), and mixture was stirred overnight at ambient temperature. Only one regioisomer, 7-(trifluoromethyl)-2,3-dihydroquinolin-4(1H)-one was converted to the oxime. The mixture was concentrated under reduced pressure and ethyl acetate (300 mL) was added. The organic layer was washed twice with water (300 mL) and brine, dried over sodium sulfate, and concentrate under reduced pressure. The residue was chromatographed on silica gel eluting with 20-70% ethyl acetate in hexane to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 2.70 (t, J=6.61 Hz, 2H), 3.19 (td, J=6.53, 1.86 Hz, 2H), 3.90 (s, 3H), 6.57 (s, 1H), 6.82 (dd, J=8.14, 1.70 Hz, 1H), 6.97 (s, 1H), 7.79 (d, J=8.14 Hz, 1H). MS (DCI) m/z 245.05 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure and ethyl acetate (300 mL)
  2. additionwas added
  3. washThe organic layer was washed twice with water (300 mL) and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrate under reduced pressure
  6. customThe residue was chromatographed on silica gel eluting with 20-70% ethyl acetate in hexane

Sources & evidence

ORD record
ord-a96d131f87494ebda95f519625a66592
Source dataset
uspto-grants-2013_01
Patent number
US08350083B2

Reaction notes

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