Hydrochloric Acid → 4-(4-Hydroxyphenyl)-3-methyl-6h-isoxazolo[3,4-d]pyridazin-7-one

HRID 221851Notes

Reaction equation

HRID 221851 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]3[C:11](=[N:16][O:17][C:18]=3[CH3:19])[C:12](=[O:15])[NH:13][N:14]=2)=[CH:5][CH:4]=1.C([S-])C.[Na+].O.Cl>CN(C=O)C>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]3[C:11](=[N:16][O:17][C:18]=3[CH3:19])[C:12](=[O:15])[NH:13][N:14]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4459711Sodium ethanethiolateHCID 441218194-(4-methoxyphenyl)-3-methylisoxazolo[3,4-d]pyridazin-7(6H)-one

Product 1

HCID 1359822734-(4-Hydroxyphenyl)-3-methyl-6h-isoxazolo[3,4-d]pyridazin-7-oneYield 53.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
100 °C

Procedure

To 1.05 g of 4-(4-methoxyphenyl)-3-methyl-6 h-isoxazolo[3,4-d]pyridazin-7-one (4.08 mmol) in 15 mL dry DMF was added 1.03 g of sodium ethanethiolate in 15 mL dry DMF at room temperature. The reaction was then heated at 100° C. for 2.5 h. Added water and 1 M HCl until acidic. Extracted the product with diethyl ether and dried the extracts with Na2SO4, filtered, and concentrated in vacuo. The product was purified via silica gel chromatography eluting with 95:5 dichloromethane:methanol to give 533 mg of 4-(4-hydroxyphenyl)-3-methyl-6 h-isoxazolo[3,4-d]pyridazin-7-one; Mp 268-276° C.; MS m/z 216 (M−N2+H).

Workup

  1. extractionExtracted the product with diethyl ether
  2. dry with materialdried the extracts with Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe product was purified via silica gel chromatography
  6. washeluting with 95:5 dichloromethane

Sources & evidence

ORD record
ord-ae890d75733941dbaeb1793767789fc2
Source dataset
uspto-grants-2012_06
Patent number
US08207168B2

Reaction notes

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