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

HRID 1852061Notes

Reaction equation

HRID 1852061 reaction equation
[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

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178517605HCID 178517605, compound

Product 1

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

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-8a9bb86fb94a436aa5da896984dfcfab
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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