Water → HCID 73630006, compound

HRID 1603013Notes

Reaction equation

HRID 1603013 reaction equation
Cl.[NH2:2][OH:3].[OH-].[K+].[F:6][C:7]1[CH:8]=[C:9]([C:15](=O)[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:10]=[CH:11][C:12]=1[O:13][CH3:14].O>C(O)C.C1(C)C=CC=CC=1>[F:6][C:7]1[CH:8]=[C:9]([C:15](=[N:2][OH:3])[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:10]=[CH:11][C:12]=1[O:13][CH3:14]

Participants

7

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 2759000HCID 2759000, compound

Product 1

HCID 73630006HCID 73630006, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

Hydroxylamine hydrochloride (3.7 g, 53.2 mmol) and potassium hydroxide (2.98 g, 53.2 mmol) were suspended in absolute ethanol (25 mL) and vigorously stirred in a 250-mL round-bottom flask equipped with a magnetic stirring bar under a dry nitrogen blanket for 30 minutes. To this, a suspension of 1-(3-fluoro-4-methoxyphenyl)-2-phenyl-ethan-1-one from Step 1 (10.0 g, 40.9 mmol) in toluene (150 mL) was added in one portion. A Dean-Stark trap and reflux condenser were added to the apparatus, and the yellow suspension was warmed to reflux. The solution was maintained at reflux 16 hours, then the suspension was cooled to room temperature. Water (100 mL) was added, and the resulting solution was extracted with ethyl acetate (2×100 mL). The combined organic solution was washed with brine (100 mL), dried over magnesium sulfate and filtered. The resulting solution was evaporated under reduced pressure to yield a crude residue. The residue was crystallized from boiling ethanol/water to yield, upon filtration and drying, 10.0 g (94%) of 1-(3-fluoro-4-methoxyphenyl)-2 phenyl-ethan-1-one oxime as ivory-colored crystals: 1H NMR (CDCl3 /300 MHz) δ 7.42 (dd, J=12.69, 2.01, 1H), 7.36-7.19 (m, 6H), 6.89 (dd, J=8.66, 8.46 HZ, 1H), 4.16 (s, 2H), 3.88 (s, 3H). 19F NMR (CDCl3 /282.2 MHz): 135.517 (m).

Workup

  1. customequipped with a magnetic stirring bar under a dry nitrogen blanket for 30 minutes
  2. additionwas added in one portion
  3. temperatureA Dean-Stark trap and reflux condenser
  4. additionwere added to the apparatus
  5. temperaturethe yellow suspension was warmed to reflux
  6. temperatureThe solution was maintained
  7. temperatureat reflux 16 hours
  8. extractionthe resulting solution was extracted with ethyl acetate (2×100 mL)
  9. washThe combined organic solution was washed with brine (100 mL)
  10. dry with materialdried over magnesium sulfate
  11. filtrationfiltered
  12. customThe resulting solution was evaporated under reduced pressure

Sources & evidence

ORD record
ord-cde37346fe984fb09b62e955fb56815c
Source dataset
uspto-grants-1999_11
Patent number
US05985902

Reaction notes

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