Phosphorus oxychloride → 7-Bromo-1-chloro-6-methoxyisoquinoline

HRID 2060364Notes

Reaction equation

HRID 2060364 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][NH:8][C:9]2=O)=[CH:4][C:3]=1[O:13][CH3:14].P(Cl)(Cl)([Cl:17])=O>>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[C:9]2[Cl:17])=[CH:4][C:3]=1[O:13][CH3:14]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 580051257-Bromo-6-methoxy-1(2H)-isoquinolinone

Product 1

HCID 595711467-Bromo-1-chloro-6-methoxyisoquinoline

Procedure

A mixture of the product from Step 2 (7-bromo-6-methoxyisoquinolin-1(2H)-one) (4.7 g, 18.5 mmol) in phosphorus oxychloride (30 mL) was heated to reflux for 2 h, cooled to RT, the volatiles evaporated and the residue partitioned between 3M NaOH and DCM. The organic phase was dried over Na2SO4, solvent evaporated and the solid triturated with Et2O (20 mL) and filtered to give a solid (3.75 g). LRMS ESI+ (M+H)+ 274.0.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 h
  3. customthe volatiles evaporated
  4. customthe residue partitioned between 3M NaOH and DCM
  5. dry with materialThe organic phase was dried over Na2SO4, solvent
  6. customevaporated
  7. customthe solid triturated with Et2O (20 mL)
  8. filtrationfiltered

Sources & evidence

ORD record
ord-17e8341d8d9d4154bc30772648a13051
Source dataset
uspto-grants-2012_10
Patent number
US08278322B2

Reaction notes

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