Methanesulfonic Acid → HCID 70978316, compound

HRID 2361601Notes

Reaction equation

HRID 2361601 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][NH:6][C:7]2=[O:12].I(C1C=CC=C(C[C:22]([O-])=[O:23])C=1CC([O-])=O)=O.CS(O)(=O)=O>CO>[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]([O:23][CH3:22])=[CH:5][NH:6][C:7]2=[O:12]

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 218898205-Chloroisoquinolin-1(2H)-oneHCID 22180138HCID 22180138, compound

Product 1

HCID 70978316HCID 70978316, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-chloroisoquinolin-1(2H)-one (3.8 g, 21.2 mmol) in methanol (70 ml) was added iodosobenzenediacetate (7.5 g, 23.4 mmol) followed by methane sulphonic acid (2.45 g, 25.5 mmol) at room temperature. The reaction mass was heated at reflux for 3 h. The solvent was evaporated and the residue was diluted with cold water. The precipitated solid was filtered, washed with water to get crude compound (3.9 g, 88%) as a light red colored solid. 1H NMR (400 MHz, CDCl3): δ ppm 8.06-8.03 (d, J=12 Hz, 1H), 7.60-7.57 (d, J=12 Hz, 1H), 7.42 (d, J=8 Hz, 1H), 7.01-6.99 (br s, 1H), 3.51 (s, 3H); MS: MS m/z 209.1 (M++1).

Workup

  1. temperatureThe reaction mass was heated
  2. temperatureat reflux for 3 h
  3. customThe solvent was evaporated
  4. additionthe residue was diluted with cold water
  5. filtrationThe precipitated solid was filtered
  6. washwashed with water

Sources & evidence

ORD record
ord-f9c7e64316e6430f8984d79bc640a106
Source dataset
uspto-grants-2014_04
Patent number
US08691757B2

Reaction notes

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