Phosphorus oxychloride → 3-(4-(Tert-butyl)phenyl)-1-chloro-6-methoxyisoquinoline

HRID 1852249

반응식

HRID 1852249 반응식
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[NH:12][C:13](=O)[C:14]3[C:19]([CH:20]=2)=[CH:18][C:17]([O:21][CH3:22])=[CH:16][CH:15]=3)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].O=P(Cl)(Cl)[Cl:26]>>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]=[C:13]([Cl:26])[C:14]3[C:19]([CH:20]=2)=[CH:18][C:17]([O:21][CH3:22])=[CH:16][CH:15]=3)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

3

반응물 2

HCID 24813Phosphorus oxychlorideHCID 709790183-(4-(tert-butyl)phenyl)-6-methoxyisoquinolin-1(2H)-one

생성물 1

HCID 866832693-(4-(Tert-butyl)phenyl)-1-chloro-6-methoxyisoquinoline수율 28%

실험 절차

A solution of 3-(4-(tert-butyl)phenyl)-6-methoxyisoquinolin-1(2H)-one (0.7 g, 2.277 mmol) in POCl3 (7 ml) was refluxed for overnight. 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 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 (10% ethyl acetate in pet ether) to get desired compound (0.21 g, 28.0%) as solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 8.34(s, 1H), 8.18-8.16 (d, J=8 Hz, 1H), 8.08-8.06 (d, J=8 Hz, 2H), 7.57-7.55 (d, J=8 Hz, 2H), 7.41 (s, 1H), 7.40-7.38 (d, J=8 Hz, 1H), 3.97 (s, 3H), 1.34 (s, 9H); MS: MS m/z 362.2 (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 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 (10% ethyl acetate in pet ether)

출처 및 근거

ORD 기록
ord-c0a156650a184eb2bbb2c3f68ed63fbc
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08957203B2

연결된 노트

불러오는 중…