Ethanol → 4-Chloro-2-methoxy-5-(1-methylcyclopropyl)aniline

HRID 588870ノート

反応式

HRID 588870 の反応式
[Cl:1][C:2]1[C:7]([C:8]2([CH3:11])[CH2:10][CH2:9]2)=[CH:6][C:5]([NH:12]C(=O)C)=[C:4]([O:16][CH3:17])[CH:3]=1.[OH-].[K+].C(O)C>O>[Cl:1][C:2]1[C:7]([C:8]2([CH3:11])[CH2:9][CH2:10]2)=[CH:6][C:5]([NH2:12])=[C:4]([O:16][CH3:17])[CH:3]=1

参加物

5

反応物 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 90455914N-[4-Chloro-2-methoxy-5-(1-methylcyclopropyl)phenyl]acetamide

生成物 1

HCID 904558234-Chloro-2-methoxy-5-(1-methylcyclopropyl)aniline収率 67.3%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A mixture of N-(4-chloro-2-methoxy-5-(1-methylcyclopropyl)phenyl)acetamide (820 mg, 3.23 mmol), KOH (1.8 g, 32.3 mmol), ethanol (40 mL) and water (20 mL) was stirred at reflux for 12 h. The reaction mixture was extracted with ethyl acetate. The combined organic layer was washed with water and brine, dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuo and the residue was purified by flash column chromatography on silica gel (ethyl acetate/petroleum ether=20:1) to afford the desired product (460 mg, 67% yield). ESI-MS m/z: 212.4[M+H]+.

後処理

  1. temperatureat reflux for 12 h
  2. extractionThe reaction mixture was extracted with ethyl acetate
  3. washThe combined organic layer was washed with water and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe residue was purified by flash column chromatography on silica gel (ethyl acetate/petroleum ether=20:1)

出典と根拠

ORDレコード
ord-0056386f1ecc487cbeac5491d8ced0cf
出典データセット
uspto-grants-2016_01
特許番号
US09227978B2

反応ノート

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