Chloride → 5-Methoxyisoquinoline

HRID 840145노트

반응식

HRID 840145 반응식
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2.[CH3:12][O-].[Na+].[Cl-]>CO.CN(C=O)C>[CH3:12][O:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2

참가 물질

6

반응물 3

HCID 312ChlorideHCID 30386Isoquinolin-5-olHCID 10942334Sodium Methoxide

생성물 1

HCID 137542835-Methoxyisoquinoline수율 56%

시약·촉매·용매 2

HCID 887Methanol용매2회HCID 6228Dimethylformamide용매

실험 절차

To a solution of 5-hydroxyisoquinoline (10 g, 69 mmol) in MeOH (100 ml) was added a solution of sodium methoxide in methanol (30% by weight, 13.8 ml, 72.4 mmol) followed by phenyltrimethylanmmonium chloride (12.4 g, 72.4 mmol). The reaction mixture was stirred at room temperature for 2 h, after which time it was filtered and the filtrate evaporated under reduced pressure to afford an oil which was dissolved in DMF (50 ml). The reaction mixture was refluxed for 2 h after which time the reaction mixture was evaporated under reduced pressure. The resulting oil was partitioned between CH2Cl2 and 1N aqueous NaOH, the organic layer was washed twice with 1N aqueous NaOH, dried over MgSO4 and evaporated under reduced pressure. The crude product was purified on silica gel eluting with EtOAc/hexane (1/1, v/v) to afford the subtitle compound as a yellow oil (6.11 g, 56%). 1H NMR (CDCl3) δ: 4.05 (3H, s), 7.00 (1H, d), 7.55 (2H, m), 8.02 (1H, d), 8.55 (1H, d), 9.22 (1H, s).

후처리

  1. filtrationafter which time it was filtered
  2. customthe filtrate evaporated under reduced pressure
  3. customto afford an oil which
  4. temperatureThe reaction mixture was refluxed for 2 h after which time the reaction mixture
  5. customwas evaporated under reduced pressure
  6. customThe resulting oil was partitioned between CH2Cl2 and 1N aqueous NaOH
  7. washthe organic layer was washed twice with 1N aqueous NaOH
  8. dry with materialdried over MgSO4
  9. customevaporated under reduced pressure
  10. customThe crude product was purified on silica gel eluting with EtOAc/hexane (1/1

출처 및 근거

ORD 기록
ord-598f68cccb4b466ea6e0699cb4226101
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06365599B1

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