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

HRID 389196

Reaction equation

HRID 389196 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 (4.7 g, 18.5 mmol) in phosphorus oxychloride (30 mL) was heated to reflux for 2 hours and cooled to RT; the volatiles were evaporated; and the residue was partitioned between 3 M NaOH and DCM. The organic phase was dried over Na2SO4; the solvent was evaporated; and the solid was triturated with Et2O (20 mL) and filtered to give the title compound (3.75 g). LRMS ESI+ (M+H)+ 274.0.

Workup

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

Sources & evidence

ORD record
ord-ea9d5e9ffeac4723bfe44db32f1fcb94
Source dataset
uspto-grants-2013_02
Patent number
US08377874B2

Linked notes

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