Water → HCID 136167191, compound

HRID 2097244Notes

Reaction equation

HRID 2097244 reaction equation
Cl.[NH2:2]O.[Cl:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[OH:15])[O:11][C:10]([CH3:16])=[C:9]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)[C:8]2=[O:25].O>N1C=CC=CC=1>[Cl:4][C:5]1[CH:6]=[C:7]([C:8]2[O:25][N:2]=[C:10]([CH3:16])[C:9]=2[C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)[C:12]([OH:11])=[CH:13][C:14]=1[OH:15]

Participants

5

Reactant 3

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 11197888HCID 11197888, compound

Product 1

HCID 136167191HCID 136167191, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Hydroxylamine hydrochloride (0.7 g, 10 mmol) was added to a suspension of 6-chloro-7-hydroxy-3-(4-methoxy-phenyl)-2-methyl-chromen-4-one [prepared analogously to Example 1, Step 2] (0.32 g, 1.0 mmol) in pyridine (4 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 4-chloro-6-[4-(4-methoxy-phenyl)-3-methyl-isoxazol-5-yl]-benzene-1,3-diol as an off-white powder (0.103 g)

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-f9c5410c999746b2bb1c8d154cc9139f
Source dataset
uspto-grants-2013_05
Patent number
US08450310B2

Reaction notes

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