Pyridine → HCID 87138672, compound

HRID 41960Notes

Reaction equation

HRID 41960 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([F:10])=[C:6]([O:11][CH3:12])[CH:5]=1)=O.Cl.[N:14]1[O:15][N:16]=[C:17]2[CH:22]=[C:21]([CH2:23][O:24][NH2:25])[CH:20]=[CH:19][C:18]=12.N1C=CC=CC=1>C(O)C>[N:14]1[O:15][N:16]=[C:17]2[CH:22]=[C:21]([CH2:23][O:24][N:25]=[C:2]([C:4]3[CH:9]=[CH:8][C:7]([F:10])=[C:6]([O:11][CH3:12])[CH:5]=3)[CH3:1])[CH:20]=[CH:19][C:18]=12

Participants

5

Reactant 3

HCID 1049PyridineHCID 27745321-(4-Fluoro-3-methoxyphenyl)ethanoneHCID 66760966O-(benzo[c][1,2,5]oxadiazol-5-ylmethyl)hydroxylamine hydrochloride

Product 1

HCID 87138672HCID 87138672, compoundYield 74.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-fluoro-3-methoxyacetophenone (0.056 g, 0.332 mmol), (benzo[c][1,2,5]oxadiazol-5-yl)methoxyamine hydrochloride (0.072 g, 0.359 mmol) and pyridine (0.10 ml, 1.24 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 dichloromethane/water. The resultant mixture was extracted with dichloromethane (×3). The combined organic phases were washed with water and brine, dried over magnesium sulphate, filtered and concentrated to a white solid. The crude product was purified by column chromatography (SiO2), eluting with 9:1 petrol/ethyl acetate, to give a 4′-fluoro-3′-methoxyacetophenone-O-[(benzo[c][1,2,5]oxadiazol-5-yl)methyl]oxime (CP9-129) as a white solid (0.078 g, 74%), m.p. 65°.

Workup

  1. temperatureat reflux under nitrogen for 4 h
  2. concentrationThe solution was concentrated to a pale yellow oil which
  3. additionwas diluted with dichloromethane/water
  4. extractionThe resultant mixture 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 a white solid
  9. customThe crude product was purified by column chromatography (SiO2)
  10. washeluting with 9:1 petrol/ethyl acetate

Sources & evidence

ORD record
ord-3f6b3d6cafb64401b07764ac7de105a4
Source dataset
uspto-grants-2013_09
Patent number
US08536157B2

Reaction notes

Loading…