Phosphorus oxychloride → HCID 86683223, compound

HRID 1852152Notes

Reaction equation

HRID 1852152 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](O)=[N:8][C:7]([C:14]([F:17])([F:16])[F:15])=[CH:6]2.O=P(Cl)(Cl)[Cl:20]>>[Cl:20][C:9]1[C:10]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:12][CH:11]=2)[CH:6]=[C:7]([C:14]([F:17])([F:16])[F:15])[N:8]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178487749HCID 178487749, compound

Product 1

HCID 86683223HCID 86683223, compoundYield 86%

Conditions

Temperature
0 °C

Procedure

A solution of 6-methoxy-3-(trifluoromethyl)isoquinolin-1-ol (271 mg, 1.114 mmol) in POCl3 (3 mL) was refluxed for 4 h. After concentration, the residue was taken into a mixture of 100 mL of DCM and 50 mL of water, cooled to 0° C., neutralized with 3 N NaOH, dried over MgSO4, concentrated and purified via silica gel chromatography (5-20% EtOAc:Hex) to give the pure product 1-chloro-6-methoxy-3-(trifluoromethyl)isoquinoline (250 mg, 0.956 mmol, 86% yield) as an orange solid. MS: MS m/z 262.1(M++1).

Workup

  1. concentrationAfter concentration
  2. additionthe residue was taken into a mixture of 100 mL of DCM and 50 mL of water
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. custompurified via silica gel chromatography (5-20% EtOAc:Hex)

Sources & evidence

ORD record
ord-f3732c9a7cf7460f9a8d18e6920df31f
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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