Water → HCID 136167197, compound

HRID 1891127Notes

Reaction equation

HRID 1891127 reaction equation
Cl.[NH2:2]O.[OH:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9](=[O:24])[C:10]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)=[C:11]([CH3:15])[O:12]2)=[CH:7][C:6]=1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.O>N1C=CC=CC=1>[CH3:23][O:22][C:19]1[CH:20]=[CH:21][C:16]([C:10]2[C:11]([CH3:15])=[N:2][O:24][C:9]=2[C:8]2[CH:7]=[C:6]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:5]([OH:4])=[CH:14][C:13]=2[OH:12])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 59264794HCID 59264794, compound

Product 1

HCID 136167197HCID 136167197, compoundYield 73.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Hydroxylamine hydrochloride (75 mg, 1.08 mmol) was added to a suspension of 7-hydroxy-3-(4-methoxy-phenyl)-2-methyl-6-phenyl-chromen-4-one (105 mg, 0.29 mmol) in pyridine (2 ml) and the mixture heated under reflux for ˜6 hrs., to give a pale yellow solution. The solution was allowed to cool and water (20 ml) added. The mixture was extracted with diethyl ether (2×10 ml). The combined extracts were washed with water (2×20 ml) and saturated aqueous sodium chloride solution (10 ml). The solution was dried over anhydrous magnesium sulphate and concentrated. The crude products were purified by column chromatography, silica, eluting with ethyl acetate/hexane (1:1), to give the title compound as an off-white powder (80 mg)

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for ˜6 hrs
  3. custom, to give a pale yellow solution
  4. temperatureto cool
  5. extractionThe mixture was extracted with diethyl ether (2×10 ml)
  6. washThe combined extracts were washed with water (2×20 ml) and saturated aqueous sodium chloride solution (10 ml)
  7. dry with materialThe solution was dried over anhydrous magnesium sulphate
  8. concentrationconcentrated
  9. customThe crude products were purified by column chromatography, silica
  10. washeluting with ethyl acetate/hexane (1:1)

Sources & evidence

ORD record
ord-ab962fdf8ba14fb7ba1e4dd6e8956f2a
Source dataset
uspto-grants-2013_08
Patent number
US08507480B2

Reaction notes

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