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

HRID 6754

반응식

HRID 6754 반응식
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

참가 물질

4

반응물 2

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

생성물 1

HCID 150619777-Methoxy-1-methyl-3,4-dihydroisoquinoline수율 45.3%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
120 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-30b35afd736244dbb5dcce6e7edbcd5b
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07084154B2

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