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

HRID 221851
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HRID 221851 반응식
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
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참가 물질

6

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

생성물 1

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

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매
2회

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온도
100 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-ae890d75733941dbaeb1793767789fc2
출처 데이터셋
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08207168B2

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