O-Methylhydroxylamine → HCID 76619013, compound

HRID 1809138Notes

Reaction equation

HRID 1809138 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8](=O)[CH2:9][C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[CH:5]=[CH:6][CH:7]=1.[NH2:17][O:18][CH3:19]>N1C=CC=CC=1>[CH3:19][O:18][N:17]=[C:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=1)[CH2:9][C:10]1[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 4113O-MethylhydroxylamineHCID 112528861-(3-FLUOROPHENYL)-2-(4-PYRIDYL)ETHANONE

Product 1

HCID 76619013HCID 76619013, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 1-(3-fluorophenyl)-2-(pyridin-4-yl)ethanone, (18) (3.6 g, 16.17 mmol) in pyridine (20 mL) was added NH2OMe (2.8 g, 33.4 mmol), at room temperature. The mixture was stirred at 80° C. for 3 h. The reaction was cooled to room temperature and quenched with water (20 mL). The aqueous layer was extracted with dichloromethane (3×, 100 ml). The pooled organic layer was dried over magnesium sulfate. The mixture was filtered. The solvents were removed under vacuum. Purification by MPLC (0 to 10% methanol in dichloromethane) gave 1-(3-fluorophenyl)-2-(pyridin-4-yl)ethanone O-methyl oxime, (19): as a oil (3.15 mg, 77% yield).

Workup

  1. customat room temperature
  2. temperatureThe reaction was cooled to room temperature
  3. customquenched with water (20 mL)
  4. extractionThe aqueous layer was extracted with dichloromethane (3×, 100 ml)
  5. dry with materialThe pooled organic layer was dried over magnesium sulfate
  6. filtrationThe mixture was filtered
  7. customThe solvents were removed under vacuum
  8. customPurification by MPLC (0 to 10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-a59bcce2741d4561b8c25168eccc34d6
Source dataset
uspto-grants-2013_01
Patent number
US08362022B2

Reaction notes

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