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

HRID 1507075ノート

反応式

HRID 1507075 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

反応条件

温度
160 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-a7348c518acd4a61846718d8cbd716b6
出典データセット
uspto-grants-2015_12
特許番号
US09221755B2

反応ノート

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