Phosphorus oxychloride → 1-Chloro-6-methyl-5-nitroisoquinoline

HRID 1668910Notes

Reaction equation

HRID 1668910 reaction equation
[CH3:1][C:2]1[C:3]([N+:14]([O-:16])=[O:15])=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=O)[NH+:7]([O-])[CH:6]=[CH:5]2.P(Cl)(Cl)([Cl:19])=O>C(Cl)(Cl)Cl>[Cl:19][C:8]1[C:9]2[C:4](=[C:3]([N+:14]([O-:16])=[O:15])[C:2]([CH3:1])=[CH:11][CH:10]=2)[CH:5]=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 86614217HCID 86614217, compound

Product 1

HCID 226222211-Chloro-6-methyl-5-nitroisoquinoline

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
70 °C

Procedure

6-Methyl-5-nitroisoquinolin-1(2H)-one-N-oxide (3.1 g, 15.2 mmol) was taken up in chloroform (100 mL) and phosphorus oxychloride (7 mL, 80 mmol) was added dropwise to the reaction. The mixture was then heated to 70° C. After 3 h, the reaction was cooled and the volatiles removed in vacuo. Residual phosphorus oxychloride was azeotroped with toluene. The residue was then dissolved in chloroform and washed with cold water, saturated NaHCO3 and brine. The organic layer was then dried with sodium sulfate and purified by column chromatography using 10 to 40% ethyl acetate in hexanes as an eluent. The title compound was obtained an off-white solid (3.4 g, 96%). MS (M+H)+ 223.

Workup

  1. temperaturethe reaction was cooled
  2. customthe volatiles removed in vacuo
  3. customResidual phosphorus oxychloride was azeotroped with toluene
  4. dissolutionThe residue was then dissolved in chloroform
  5. washwashed with cold water, saturated NaHCO3 and brine
  6. dry with materialThe organic layer was then dried with sodium sulfate
  7. custompurified by column chromatography

Sources & evidence

ORD record
ord-0dae45d12c564dd1a244c5c20a20505b
Source dataset
uspto-grants-2011_08
Patent number
US07989461B2

Reaction notes

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