Phosphorus oxychloride → 1-Chloro-7-fluoro-4-methoxyisoquinoline

HRID 2361612노트

반응식

HRID 2361612 반응식
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([O:13][CH3:14])=[CH:7][NH:8][C:9]2=O)=[CH:4][CH:3]=1.O=P(Cl)(Cl)[Cl:17]>>[Cl:17][C:9]1[C:10]2[C:5](=[CH:4][CH:3]=[C:2]([F:1])[CH:11]=2)[C:6]([O:13][CH3:14])=[CH:7][N:8]=1

참가 물질

3

반응물 2

HCID 24813Phosphorus oxychlorideHCID 222502317-Fluoro-4-methoxyisoquinolin-1-OL

생성물 1

HCID 222502381-Chloro-7-fluoro-4-methoxyisoquinoline수율 24%

실험 절차

A solution of 7-fluoro-4-methoxyisoquinolin-1(2H)-one (11 g, 56.9 mmol) in POCl3 (100 ml) was refluxed for 18 h. The solvent was evaporated under reduced pressure and the residue was diluted with cold water. The aqueous solution was basified by solid sodium carbonate and extracted with ethyl acetate. The combine organic layer was dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to get crude compound. The crude compound was purified by silica gel chromatography (20% ethyl acetate in pet ether) to get desired compound (2.9 g, 24%) as off-white solid. 1H NMR (400 MHz, CDCl3): δ ppm 8.36-8.32 (m, 1H), 7.93-7.90 (m, 1H), 7.88 (s, 1H), 7.70-7.65 (m, 1H), 4.11 (s, 3H); MS: MS m/z 212.1 (M++1).

후처리

  1. customThe solvent was evaporated under reduced pressure
  2. additionthe residue was diluted with cold water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combine organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customto get crude compound
  8. customThe crude compound was purified by silica gel chromatography (20% ethyl acetate in pet ether)

출처 및 근거

ORD 기록
ord-446add8215fc470c84b89013f3dbed66
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08691757B2

반응 노트

불러오는 중…