Isatoic Anhydride → 2-Amino-N-methylbenzamide

HRID 2424375Notes

Reaction equation

HRID 2424375 reaction equation
[C:1]12[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH:6]C(=O)O[C:2]2=[O:3].[CH3:13][NH2:14].O1CCCC1>O>[NH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:1]=1[C:2]([NH:14][CH3:13])=[O:3]

Participants

4

Reactant 2

HCID 8359Isatoic AnhydrideHCID 66615946Methylamine tetrahydrofuran

Product 1

HCID 3080722-Amino-N-methylbenzamideYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 16.3 g (100 mmol) of isatoic anhydride in 100 mL of H2O is added portionwise 100 mL of 2N methylamine-tetrahydrofuran solution (200 mmol) at room temperature. The reaction mixture is stirred for 1 hour and then extracted with AcOEt. The organic layer is washed with H2O and brine, dried over Na2SO4, and concentrated under reduced pressure to give 13.79 g of desired product, 2-amino-N-methyl-benzamide (92 mmol, 92%) as colorless solid.

Workup

  1. extractionextracted with AcOEt
  2. washThe organic layer is washed with H2O and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-72b2976e263c421fad6421631fcedb39
Source dataset
uspto-grants-2011_06
Patent number
US07964592B2

Reaction notes

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