Methyl iodide → 2,4-Dimethoxy-6-methylamino-benzamide

HRID 336732Notes

Reaction equation

HRID 336732 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[C:7]([O:13][CH3:14])[C:3]=1[C:4]([NH2:6])=[O:5].[CH3:15]I>>[CH3:14][O:13][C:7]1[CH:8]=[C:9]([O:11][CH3:12])[CH:10]=[C:2]([NH:1][CH3:15])[C:3]=1[C:4]([NH2:6])=[O:5]

Participants

3

Reactant 2

HCID 6328Methyl iodideHCID 203490162-Amino-4,6-dimethoxybenzamide

Product 1

HCID 666617532,4-Dimethoxy-6-methylamino-benzamideYield 50.4%

Conditions

Temperature
110 °C

Procedure

2-Amino-4,6-dimethoxybenzamide (0.5 g, 2.55 mmol) and methyl iodide (0.17 mL, 2.81 mmol) were mixed in a closed bomb and heated at 110° C. for 14 h. The compound was washed with a dichloromethane-methanol mixture. After removing the solvent, the crude was purified by silica gel column chromatography (40 g) employing 1-5% methanol in dichloromethane to give 2,4-dimethoxy-6-methylamino-benzamide (0.027 g, 50.4%).

Workup

  1. washThe compound was washed with a dichloromethane-methanol mixture
  2. customAfter removing the solvent
  3. customthe crude was purified by silica gel column chromatography (40 g)

Sources & evidence

ORD record
ord-f3fa9d8e8790430b927f1580fa82b864
Source dataset
uspto-grants-2014_11
Patent number
US08889698B2

Reaction notes

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