Water → HCID 73630006, compound

HRID 343057Notes

Reaction equation

HRID 343057 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 stirred 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. The yellow suspension was warmed to reflux for 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 1-(3-fluoro-4-methoxyphenyl)-2 phenyl-ethan-1-one oxime as ivory-colored crystals (10.0 g, 94%): 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. additionwas added in one portion
  2. temperatureThe yellow suspension was warmed
  3. temperatureto reflux for 16 hours
  4. extractionthe resulting solution was extracted with ethyl acetate (2×100 mL)
  5. washThe combined organic solution was washed with brine (100 mL)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customThe resulting solution was evaporated under reduced pressure

Sources & evidence

ORD record
ord-2653c540e34848de87ecf107ba8a96ae
Source dataset
uspto-grants-1999_01
Patent number
US05859257

Reaction notes

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