Water → HCID 136167191, compound

HRID 1891128Notes

Reaction equation

HRID 1891128 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-fdec1cd8664b4bed914ccf6ef67c0f09
Source dataset
uspto-grants-2013_08
Patent number
US08507480B2

Reaction notes

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