Methyl iodide → N-Methylisatoic anhydride

HRID 2221372Notes

Reaction equation

HRID 2221372 reaction equation
CI.S([O:8][CH3:9])(OC)(=O)=O.[C:10]12[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=1)[NH:15][C:14](=O)[O:13][C:11]2=[O:12]>>[CH3:14][N:15]1[C:9](=[O:8])[O:13][C:11](=[O:12])[C:10]2=[CH:20][CH:19]=[CH:18][CH:17]=[C:16]12

Participants

4

Reactant 3

HCID 6328Methyl iodideHCID 6497Dimethyl SulfateHCID 8359Isatoic Anhydride

Product 1

HCID 25160N-Methylisatoic anhydride

Procedure

N-methylation could be achieved by adding an alkylation agent. Preferably methyl iodide or dimethyl sulfate in a molar ratio, relative to isatoic anhydride, from 1 to 5, preferably 1.5, at a temperature from 10-40° C. In the case of a methylating agent, the intermediate N-methylisatoic anhydride could be isolated by filtration as a colourless crystalline compound by adding 2 parts of water to the reaction mixture. Identification was established by compare HPLC chromatograms with authentic material (supplied by Aldrich).

Workup

  1. additionby adding an alkylation agent
  2. customfrom 10-40° C

Sources & evidence

ORD record
ord-7693f8afad884d0a828423defa551764
Source dataset
uspto-grants-2008_05
Patent number
US07368592B1

Reaction notes

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