Sodium Hydroxide → 4-(2-Methoxyethoxy)-3-(2-methyl-2H-pyrazol-3-yl)aniline

HRID 1191627노트

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HRID 1191627 반응식
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12]C(=O)C)=[CH:8][C:7]=1[C:16]1[N:17]([CH3:21])[N:18]=[CH:19][CH:20]=1.[OH-].[Na+]>CO.O>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][C:7]=1[C:16]1[N:17]([CH3:21])[N:18]=[CH:19][CH:20]=1

참가 물질

5

반응물 2

HCID 14798Sodium HydroxideHCID 67265798N-(4-(2-methoxyethoxy)-3-(2-methyl-2H-pyrazol-3-yl)phenyl)acetamide

생성물 1

HCID 577866324-(2-Methoxyethoxy)-3-(2-methyl-2H-pyrazol-3-yl)aniline수율 93.4%

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

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온도
160 °C

실험 절차

To a suspension of N-(4-(2-methoxyethoxy)-3-(2-methyl-2H-pyrazol-3-yl)phenyl)acetamide (289 mg, 1.0 mmol) in MeOH (3 mL) was added a solution of sodium hydroxide (240 mg, 6.0 mmol) in water (0.4 mL) and the mixture was stirred at 160° C. in a microwave oven. After 30 minutes, the mixture was allowed to cool to room temperature, and the solvent was removed under reduced pressure. The residue was taken up in water, and extracted three times with dichloromethane. The extracts were combined, dried with sodium sulfate, filtered, and evaporated to dryness to afford the title compound (231 mg, 93% yield) as a brown oil which was used without further purification. LCMS m/z (%) 248.1 (M+H, 100%). 1H NMR (400 MHz, DMSO-d6) δ 3.19 (s, 3H) 3.48-3.53 (m, 2H) 3.63 (s, 3H) 3.89-3.96 (m, 2H) 4.81 (s, 2H) 6.16 (d, J=1.77 Hz, 1H) 6.48 (d, J=3.03 Hz, 1H) 6.62 (dd, J=8.72, 2.91 Hz, 1H) 6.86 (d, J=8.84 Hz, 1H) 7.39 (d, J=1.77 Hz, 1H).

후처리

  1. temperatureto cool to room temperature
  2. customthe solvent was removed under reduced pressure
  3. extractionextracted three times with dichloromethane
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness

출처 및 근거

ORD 기록
ord-13e704e1b0044a249a630f8a1805805a
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680119B2

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