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

HRID 1663640

反応式

HRID 1663640 の反応式
[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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-01981ca3befd4c06a2ddd29226793152
出典データセット
uspto-grants-2011_10
特許番号
US08034812B2

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