Pyridine → 1-(3-hydroxy-4-methoxyphenyl)ethanone-O-[(benzo[c][1,2,5]oxadiazol-5-yl)methyl]oxime

HRID 41956

Reaction equation

HRID 41956 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([OH: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]([O:10][CH3:11])=[C:6]([OH:12])[CH:5]=3)[CH3:1])[CH:20]=[CH:19][C:18]=12

Participants

5

Reactant 3

HCID 1049PyridineHCID 956931-(3-Hydroxy-4-methoxyphenyl)ethanoneHCID 66760966O-(benzo[c][1,2,5]oxadiazol-5-ylmethyl)hydroxylamine hydrochloride

Product 1

HCID 1317308411-(3-hydroxy-4-methoxyphenyl)ethanone-O-[(benzo[c][1,2,5]oxadiazol-5-yl)methyl]oximeYield 90.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-hydroxy-4-methoxyacetophenone (0.070 g, 0.421 mmol), (benzo[c][1,2,5]oxadiazol-5-yl)methoxyamine hydrochloride (0.126 g, 0.625 mmol) and pyridine (0.16 ml, 1.98 mmol) in ethanol (6 ml) was stirred at reflux under nitrogen for 4 h and cooled to room temperature. The solution was concentrated to a yellow oil which was diluted with water. The resultant suspension was extracted with dichloromethane (×3). The combined organic phases were washed with water, dried over magnesium sulphate, filtered and concentrated to a yellow oil. The crude product was purified by column chromatography (SiO2), eluting with 8:2 petrol/ethyl acetate, to give a slightly sticky solid which was further triturated with petroleum spirit (40-60°), to give 1-(3-hydroxy-4-methoxyphenyl)ethanone-O -[(benzo[c][1,2,5]oxadiazol-5-yl)methyl]oxime (CP9-33) as a light yellow solid (0.119 g, 90%).

Workup

  1. temperatureat reflux under nitrogen for 4 h
  2. concentrationThe solution was concentrated to a 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
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated to a yellow oil
  9. customThe crude product was purified by column chromatography (SiO2)
  10. washeluting with 8:2 petrol/ethyl acetate
  11. customto give a slightly sticky solid which
  12. customwas further triturated with petroleum spirit (40-60°)

Sources & evidence

ORD record
ord-5e2e2cf38815438bac726ffa7b23f1b6
Source dataset
uspto-grants-2013_09
Patent number
US08536157B2

Linked notes

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