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

HRID 1852061ノート

反応式

HRID 1852061 の反応式
[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

参加物

3

反応物 2

HCID 24813Phosphorus oxychlorideHCID 178517605HCID 178517605、化合物

生成物 1

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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8a9bb86fb94a436aa5da896984dfcfab
出典データセット
uspto-grants-2015_02
特許番号
US08957203B2

反応ノート

読み込み中…