Methanesulfonic Acid → HCID 86687433, compound

HRID 1473391Notes

Reaction equation

HRID 1473391 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][CH:6]=[CH:5]2.CS(O)(=O)=O.[C:18](O)(=[O:20])C.C(O)(=O)C.I(C1C=CC=CC=1)=O>CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][CH:6]=[C:5]2[O:20][CH3:18]

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 158851826-Bromoisoquinolin-1(2H)-oneHCID 73357407Acetic acid;iodosylbenzene

Product 1

HCID 86687433HCID 86687433, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
0 °C

Procedure

A round bottom flask was charged with 6-bromo-2h-isoquinolin-1-one (1.0 g, 4.46 mmol), methanol (8 mL), and methanesulfonic acid (0.290 ml, 4.46 mmol) and the flask was cooled to 0° C. In a separate flask, iodosobenzene diacetate (1.581 g, 4.91 mmol) was dissolved in methanol (8 mL) and added to the reaction. The reaction was warmed to room temperature and stirred for one hour, then heated to 50° C. and stirred overnight. The reaction was concentrated and triturated with isopropanol. The solution was stirred for 10 minutes, then filtered. The solids were washed with isopropanol and vacuum dried to afford 6-bromo-4-methoxyisoquinolin-1(2H)-one as a tan solid. (ESI) 254.1 (M+H

Workup

  1. additionadded to the reaction
  2. temperatureThe reaction was warmed to room temperature
  3. temperatureheated to 50° C.
  4. stirringstirred overnight
  5. concentrationThe reaction was concentrated
  6. customtriturated with isopropanol
  7. stirringThe solution was stirred for 10 minutes
  8. filtrationfiltered
  9. washThe solids were washed with isopropanol and vacuum
  10. customdried

Sources & evidence

ORD record
ord-daccdf93b5ac454ab8f9dbbb58e42a8b
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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