O-Methylhydroxylamine → HCID 76619013, compound

HRID 1027682Notes

Reaction equation

HRID 1027682 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-b69521ec2a4c4961b388692c22138fda
Source dataset
uspto-grants-2014_05
Patent number
US08735399B2

Reaction notes

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