Phosphorus oxychloride → Methyl 1-chloroisoquinoline-5-carboxylate

HRID 1051273노트

반응식

HRID 1051273 반응식
[CH3:1][O:2][C:3]([C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH:7]=[CH:8][N+:9]([O-])=[CH:10]2)=[O:4].O=P(Cl)(Cl)[Cl:18]>ClCCl>[Cl:18][C:10]1[C:11]2[CH:12]=[CH:13][CH:14]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[C:6]=2[CH:7]=[CH:8][N:9]=1

참가 물질

4

반응물 2

HCID 24813Phosphorus oxychlorideHCID 1180908815-(Methoxycarbonyl)isoquinoline 2-oxide

생성물 1

HCID 72213626Methyl 1-chloroisoquinoline-5-carboxylate수율 86%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
90 °C

실험 절차

5-(Methoxycarbonyl)isoquinoline 2-oxide (2 g, 9.84 mmol) obtained in Step (4) of Preparation Example 1 was dissolved in dichloromethane (20 mL), added with POCl3 (20 mL) at room temperature, and stirred for 4 hours or more at 90° C. The temperature of the reaction mixture was lowered to room temperature, followed by quenching with distilled water. The reaction mixture was diluted with dichloromethane, and washed with a saturated aqueous sodium bicarbonate solution and saline. The organic layer thus obtained was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain the title compound (1.86 g, 86%).

후처리

  1. customwas lowered to room temperature
  2. customby quenching with distilled water
  3. additionThe reaction mixture was diluted with dichloromethane
  4. washwashed with a saturated aqueous sodium bicarbonate solution and saline
  5. customThe organic layer thus obtained
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-51f304266d784ea59cc32b001902bdf9
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09388165B2

반응 노트

불러오는 중…