Methanesulfonic Acid → HCID 178493786, compound

HRID 1852106Notes

Reaction equation

HRID 1852106 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([OH:12])=[N:7][CH:6]=[CH:5]2.[C:13](O)(=[O:15])C.C(O)(=O)C.IC1C=CC=CC=1.CS(O)(=O)=O>CO>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([OH:12])=[N:7][CH:6]=[C:5]2[O:15][CH3:13]

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 12217721Iodo benzene diacetateHCID 178517673HCID 178517673, compound

Product 1

HCID 178493786HCID 178493786, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

6-fluoroisoquinolin-1-ol (1 g, 6.13 mmol), iodobenzene diacetate (2.172 g, 6.74 mmol) and MeOH (15 ml) were added to a sealed tube. To the mixture was added methanesulfonic acid (0.477 ml, 7.36 mmol). The threaded stopper was affixed to the vessel and the mixture was heated first to 70° C. for 4 h and then to 130° C. for 3 h. The mixture was concentrated in vacuo to remove half of methanol, then 5 mL of water was added and the solid was collected by filtration and washed thoroughly with 1:1 methanol/water then dried in vacuo to give 6-fluoro-4-methoxyisoquinolin-1-ol (800 mg, 68% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.27 (dd, J=9.0, 5.8 Hz, 1H), 7.49 (dd, J=10.0, 2.5 Hz, 1H), 7.46-7.42 (m, 1H), 6.83 (d, J=6.3 Hz, 1H), 3.81 (s, 3H); MS m/z 194.1 (M++1).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customto remove half of methanol
  3. addition5 mL of water was added
  4. filtrationthe solid was collected by filtration
  5. washwashed thoroughly with 1:1 methanol/water
  6. customthen dried in vacuo

Sources & evidence

ORD record
ord-821f0150a3dc4f8982061e791e3e599e
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

Loading…