3,5-Dimethoxyaniline → 3-Amino-5-methoxyphenol

HRID 1616944ノート

反応式

HRID 1616944 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[C:8]([O:10]C)[CH:9]=1)[NH2:6].C[S-].[Na+]>CN1CCCC1=O>[NH2:6][C:5]1[CH:7]=[C:8]([OH:10])[CH:9]=[C:3]([O:2][CH3:1])[CH:4]=1

参加物

4

反応物 2

HCID 663013,5-DimethoxyanilineHCID 4378561Sodium methanethiolate

生成物 1

HCID 119535163-Amino-5-methoxyphenol収率 60.1%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
140 °C

実験手順

3,5-Dimethoxyaniline (9.97 g, 65.1 mmol) and sodium methyl mercaptide (9.1 g, 130 mmol) were dissolved in N-methylpyrrolidinone (60 ml). The reaction mixture was stirred at 140° C. for 1 h. After cooling to room temperature, the reaction mixture was partitioned between ethyl acetate and saturated aqueous Na2HPO4. The layers were separated and the organic layer was washed with water, dried over MgSO4 and the solvent was evaporated. The residue was purified by flash chromatography on silica gel eluting with 50% EtOAc/hexanes to afford 3-amino-5-methoxyphenol (5.44 g). MS m/z: 140 [M+H]+

後処理

  1. temperatureAfter cooling to room temperature
  2. customthe reaction mixture was partitioned between ethyl acetate and saturated aqueous Na2HPO4
  3. customThe layers were separated
  4. washthe organic layer was washed with water
  5. dry with materialdried over MgSO4
  6. customthe solvent was evaporated
  7. customThe residue was purified by flash chromatography on silica gel eluting with 50% EtOAc/hexanes

出典と根拠

ORDレコード
ord-d4fd153c63bb4d4387a79c5f53a4f90f
出典データセット
uspto-grants-2014_07
特許番号
US08765779B2

反応ノート

読み込み中…