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

HRID 2045703Notes

Reaction equation

HRID 2045703 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. After 2 h, the mixture was cooled to RT; the volatiles were evaporated, and the residue was partitioned between 3M NaOH and DCM. The organic phase was dried over Na2SO4; solvent was evaporated; and the solid was triturated with Et2O (20 mL) and filtered to give a solid (3.75 g). LRMS ESI+ (M+H)+274.0.

Workup

  1. temperaturewas heated to reflux
  2. customthe volatiles were evaporated
  3. customthe residue was partitioned between 3M NaOH and DCM
  4. dry with materialThe organic phase was dried over Na2SO4
  5. customsolvent was evaporated
  6. customand the solid was triturated with Et2O (20 mL)
  7. filtrationfiltered

Sources & evidence

ORD record
ord-00308b1052d444d38b285009291689d4
Source dataset
uspto-grants-2013_11
Patent number
US08591878B2

Reaction notes

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