Phosphorus oxychloride → 7-Chloro-2,3-dihydro[1,4]dioxino[2,3-f]isoquinoline

HRID 1852061노트

반응식

HRID 1852061 반응식
[O:1]1[C:6]2=[C:7]3[C:12](=[CH:13][CH:14]=[C:5]2[O:4][CH2:3][CH2:2]1)[C:11](O)=[N:10][CH:9]=[CH:8]3.O=P(Cl)(Cl)[Cl:18]>>[Cl:18][C:11]1[C:12]2[C:7](=[C:6]3[O:1][CH2:2][CH2:3][O:4][C:5]3=[CH:14][CH:13]=2)[CH:8]=[CH:9][N:10]=1

참가 물질

3

반응물 2

HCID 24813Phosphorus oxychlorideHCID 178517605HCID 178517605, 화합물

생성물 1

HCID 218898217-Chloro-2,3-dihydro[1,4]dioxino[2,3-f]isoquinoline

실험 절차

A solution of 2,3-dihydro-[1,4]dioxino[2,3-f]isoquinolin-7-ol (5 g, 24.61 mmol) in POCl3 (50 mL) was refluxed for 14 h. After Concentration, the residue was taken into the mixture of DCM and 4N NaOH solution. The organic phase was collected and dried over sodium sulfate, filtered, then concentrated under vacuum. The crude material was purified by silica gel chromatography using 20% EtOAc/Hexanes as eluent to give 4 g of the desired product 7-chloro-2,3-dihydro-[1,4]dioxino[2,3-f]isoquinoline as a solid. 1H NMR (400 Hz, CDCl3) δ ppm 4.42 (m, 4H), 7.24 (d, J=9.05 Hz, 1H), 7.77 (d, J=5.87 Hz, 1H), 7.84 (d, J=9.05 Hz, 1H), 8.18 (d, J=5.87 Hz, 1H); MS: (M+H)+ 222.

후처리

  1. concentrationAfter Concentration
  2. additionthe residue was taken into the mixture of DCM and 4N NaOH solution
  3. customThe organic phase was collected
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe crude material was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-8a9bb86fb94a436aa5da896984dfcfab
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08957203B2

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