Phosphorus oxychloride → 7-Methoxy-1-methyl-3,4-dihydroisoquinoline

HRID 6754

反応式

HRID 6754 の反応式
P(Cl)(Cl)(Cl)=O.[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][NH:16][C:17](=O)[CH3:18])=[CH:10][CH:9]=1>C(#N)C>[CH3:6][O:7][C:8]1[CH:13]=[C:12]2[C:11]([CH2:14][CH2:15][N:16]=[C:17]2[CH3:18])=[CH:10][CH:9]=1

参加物

4

反応物 2

HCID 24813Phosphorus oxychlorideHCID 584258N-(2-(4-Methoxyphenyl)ethyl)acetamide

生成物 1

HCID 150619777-Methoxy-1-methyl-3,4-dihydroisoquinoline収率 45.3%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
120 °C

実験手順

Phosphorus oxychloride (22.5 mL) was added to a solution of N-[2-(4-methoxy-phenyl)-ethyl]-acetamide (6.5 g) in acetonitrile (200 mL). The mixture was heated at 120° C. in a sealed tube for 16 h. The solvent was evaporated. The residue was dissolved in dichloromethane (200 mL) and washed with aqueous sodium bicarbonate (saturated, 100 mL) and brine (100 mL). The dichloromethane layer was dried over sodium sulfate, filtered and evaporated. The crude product was purified by column chromatography (5% methanol in dichloromethane) to afford 7-methoxy-1-methyl-3,4-dihydro-isoquinoline (2.67 g).

後処理

  1. customThe solvent was evaporated
  2. dissolutionThe residue was dissolved in dichloromethane (200 mL)
  3. washwashed with aqueous sodium bicarbonate (saturated, 100 mL) and brine (100 mL)
  4. dry with materialThe dichloromethane layer was dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified by column chromatography (5% methanol in dichloromethane)

出典と根拠

ORDレコード
ord-30b35afd736244dbb5dcce6e7edbcd5b
出典データセット
uspto-grants-2006_08
特許番号
US07084154B2

関連ノート

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