4-Aminophenol → HCID 57541500、化合物

HRID 1184941ノート

反応式

HRID 1184941 の反応式
[CH:1]1[C:6]([NH2:7])=[CH:5][CH:4]=[C:3]([OH:8])[CH:2]=1.CC(C)([O-])C.[K+].Cl[C:16]1[CH:21]=[CH:20][N:19]=[C:18]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[NH2:7][C:6]1[CH:5]=[CH:4][C:3]([O:8][C:16]2[CH:21]=[CH:20][N:19]=[C:18]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH:17]=2)=[CH:2][CH:1]=1

参加物

7

反応物 4

HCID 4034-AminophenolHCID 11430Potassium CarbonateHCID 11806045tert-Butyl 4-chloropicolinateHCID 23665647Potassium tert-butoxide

生成物 1

HCID 57541500HCID 57541500、化合物収率 60%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

At room temperature, p-aminophenol (0.51 g, 4.70 mmol, 1 eq) was dissolved in N,N-dimethylformamide (10 mL). To the resulted solution, potassium tert-butoxide (0.53 g, 4.70 mmol, 1 eq) was added in portions and the resulted mixture was stirred for 0.5 hours. Tert-butyl 4-chloropicolinate (1 g, 4.70 mmol, 1 eq) and potassium carbonate (45 mg, 0.33 mmol, 0.07 eq) were added, and the mixture was heated to 80° C. and stirred for 2 hours. The mixture was cooled to room temperature and ethyl acetate (50 mL) was added. The mixture was filtered to remove the undissolved material and the filtrate was washed with saturated brine (20 mL×2). The organic phase was dried over anhydrous sodium sulfate, concentrated under reduced pressure to remove the solvent. The residue was purified by column chromatography (dicloromethane:ethyl acetate=30:1) to give the title compound (805 mg, purity 96%, yield 60%).

後処理

  1. stirringstirred for 2 hours
  2. temperatureThe mixture was cooled to room temperature
  3. filtrationThe mixture was filtered
  4. customto remove the undissolved material
  5. washthe filtrate was washed with saturated brine (20 mL×2)
  6. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customto remove the solvent
  9. customThe residue was purified by column chromatography (dicloromethane:ethyl acetate=30:1)

出典と根拠

ORDレコード
ord-3ad240bd14224c9099fe974445689efb
出典データセット
uspto-grants-2014_03
特許番号
US08669369B2

反応ノート

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