Pyridine → 3'-Fluoro-4'-hydroxyacetophenone-o-[(benzo[c][1,2,5]oxadiazol-5-yl)methyl]oxime

HRID 41959Notes

Reaction equation

HRID 41959 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([F:11])[CH:5]=1)=O.Cl.[N:13]1[O:14][N:15]=[C:16]2[CH:21]=[C:20]([CH2:22][O:23][NH2:24])[CH:19]=[CH:18][C:17]=12.N1C=CC=CC=1>C(O)C>[N:13]1[O:14][N:15]=[C:16]2[CH:21]=[C:20]([CH2:22][O:23][N:24]=[C:2]([C:4]3[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([F:11])[CH:5]=3)[CH3:1])[CH:19]=[CH:18][C:17]=12

Participants

5

Reactant 3

HCID 1049PyridineHCID 27373251-(3-Fluoro-4-hydroxyphenyl)ethan-1-oneHCID 66760966O-(benzo[c][1,2,5]oxadiazol-5-ylmethyl)hydroxylamine hydrochloride

Product 1

HCID 1363498273'-Fluoro-4'-hydroxyacetophenone-o-[(benzo[c][1,2,5]oxadiazol-5-yl)methyl]oximeYield 82%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-fluoro-4-hydroxyacetophenone (0.061 g, 0.398 mmol), (benzo[c][1,2,5]oxadiazol-5-yl)methoxyamine hydrochloride (0.095 g, 0.470 mmol) and pyridine (0.13 ml, 1.61 mmol) in ethanol (5 ml) was stirred at reflux under nitrogen for 4 h and cooled to room temperature. The solution was concentrated to a pale yellow oil which was diluted with water. The resultant suspension was extracted with dichloromethane (×3). The combined organic phases were washed with water and brine, dried over magnesium sulphate, filtered and concentrated to an off-white solid. The crude product was purified by column chromatography (SiO2), eluting with 9:1 petrol/ethyl acetate, to give a pale beige solid which was further washed with petrol/dichloromethane to give 3′-fluoro-4′-hydroxyacetophenone-O-[(benzo[c][1,2,5]oxadiazol-5-yl)methyl]oxime (CP9-128) as a pale beige solid (0.098 g, 82%), m.p. 139-140°.

Workup

  1. temperatureat reflux under nitrogen for 4 h
  2. concentrationThe solution was concentrated to a pale yellow oil which
  3. additionwas diluted with water
  4. extractionThe resultant suspension was extracted with dichloromethane (×3)
  5. washThe combined organic phases were washed with water and brine
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated to an off-white solid
  9. customThe crude product was purified by column chromatography (SiO2)
  10. washeluting with 9:1 petrol/ethyl acetate
  11. customto give a pale beige solid which
  12. washwas further washed with petrol/dichloromethane

Sources & evidence

ORD record
ord-c368cd9cf719461a92018c0252fce348
Source dataset
uspto-grants-2013_09
Patent number
US08536157B2

Reaction notes

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