Methanesulfonic Acid → N-(Pyridin-3-yl)-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzamide (methanesulfonate)

HRID 1830412Notes

Reaction equation

HRID 1830412 reaction equation
[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[N:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH:12][C:13](=[O:38])[C:14]2[CH:19]=[C:18]([CH2:20][C:21]3[C:22](=[O:33])[C:23]([O:31][CH3:32])=[C:24]([O:29][CH3:30])[C:25](=[O:28])[C:26]=3[CH3:27])[CH:17]=[CH:16][C:15]=2[O:34]C(=O)C)[CH:7]=1>CO>[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[N:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH:12][C:13](=[O:38])[C:14]2[CH:19]=[C:18]([CH2:20][C:21]3[C:22](=[O:33])[C:23]([O:31][CH3:32])=[C:24]([O:29][CH3:30])[C:25](=[O:28])[C:26]=3[CH3:27])[CH:17]=[CH:16][C:15]=2[OH:34])[CH:7]=1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 22054295N-(Pyridin-3-yl)-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzamide

Product 1

HCID 86593099N-(Pyridin-3-yl)-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-hydroxybenzamide (methanesulfonate)Yield 82%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methanesulfonic acid (0.00732 g, 0.0762 mmol) was added to a methanol solution (2 ml) of N-(pyridin-3-yl)-5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzamide (0.0327 g, 0.0726 mmol), and the solvent was removed by distillation. The obtained residue was recrystallized from a mixed solvent of methanol, hexane and toluene (1:2:0.2) to obtain the titled compound (0.030 g, 0.0595 mmol, 82%).

Workup

  1. customthe solvent was removed by distillation
  2. customThe obtained residue was recrystallized from a mixed solvent of methanol, hexane and toluene (1:2:0.2)

Sources & evidence

ORD record
ord-3fa3a82733654a9887f1972f9ef54823
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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