Sulfuric acid magnesium salt (1:1) → 3-{[(1,3-dimethyl-1H-pyrazol-5-yl)methyl]amino}-4-methylphenol

HRID 1667825

반응식

HRID 1667825 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH:7][C:8]1[CH:9]=[CH:10][C:11]([CH3:24])=[C:12]([NH:14][C:15]([C:17]2[N:21]([CH3:22])[N:20]=[C:19]([CH3:23])[CH:18]=2)=O)[CH:13]=1.S([O-])([O-])(=O)=O.[Na+].[Na+].S([O-])([O-])(=O)=O.[Mg+2]>O1CCCC1>[CH3:22][N:21]1[C:17]([CH2:15][NH:14][C:12]2[CH:13]=[C:8]([OH:7])[CH:9]=[CH:10][C:11]=2[CH3:24])=[CH:18][C:19]([CH3:23])=[N:20]1

참가 물질

6

반응물 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 57505436N-(5-hydroxy-2-methylphenyl)-1,3-dimethyl-1H-pyrazole-5-carboxamide

생성물 1

HCID 575054353-{[(1,3-dimethyl-1H-pyrazol-5-yl)methyl]amino}-4-methylphenol수율 52%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of 3-amino-4-methylphenol (930 mg, 7.5 mmol) in N,N-dimethylacetamide (10 mL) was added a solution of 1,3-dimethyl-1H-pyrazole-5-carbonylchloride (1370 mg, 8.7 mmol) in N, N-dimethylacetamide (5 mL), and the mixture was stirred at 0° C. for 20 min. To the mixture were added ethyl acetate/tetrahydrofuran, saturated aqueous sodium hydrogencarbonate solution, and the aqueous layer was extracted 4 times with ethyl acetate/tetrahydrofuran. Combined organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and filtrated. The filtrate was concentrated under reduced pressure, and the residue was washed with ethyl acetate/hexane to give N-(5-hydroxy-2-methylphenyl)-1,3-dimethyl-1H-pyrazole-5-carboxamide (1170 mg, 63%) as a white solid. To a suspension of lithium aluminum hydride (1130 mg, 24 mmol) in tetrahydrofuran (35 mL) was slowly added dropwise a solution of N-(5-hydroxy-2-methylphenyl)-1,3-dimethyl-1H-pyrazole-5-carboxamide (1170 mg, 4.8 mmol) in tetrahydrofuran (10 mL) under ice-cooling. After dropwise addition, the reaction mixture was heated under reflux for 5 hr. A saturated aqueous sodium sulfate solution was added to the mixture under cooling, magnesium sulfate was added and the insoluble material was filtrated. The filtrate was concentrated under reduced pressure, and the residue was washed with ethyl acetate/hexane to give the title compound (570 mg, 52%) as a white solid.

후처리

  1. temperaturecooling
  2. additionAfter dropwise addition
  3. temperaturethe reaction mixture was heated
  4. temperatureunder reflux for 5 hr
  5. temperatureunder cooling
  6. filtrationthe insoluble material was filtrated
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. washthe residue was washed with ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-82f4e27a6ea34fe399211eb2afe48088
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08044049B2

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