Sodium Bicarbonate → 4-Aminoisophthalamide
Reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([NH2:10])=[O:9])=[CH:6][C:5]=1[C:13]([NH2:15])=[O:14])([O-])=O.C(=O)(O)[O-].[Na+]>C(O)C>[NH2:1][C:4]1[CH:12]=[CH:11][C:7]([C:8]([NH2:10])=[O:9])=[CH:6][C:5]=1[C:13]([NH2:15])=[O:14]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
To a solution of 4-nitroisophthalamide (6.0 g (28.7 mmol) in ethanol (150.0 ml), stannous chloride (20.02 g (86.1 mmol) was added and the mixture was stirred at 70° C. overnight. After cooling, the reaction mixture was neutralized with a saturated aqueous sodium bicarbonate solution, and insolubles formed were removed by filtration. The filtrate was extracted with ethyl acetate and the extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 2.59 g (50%) of 4-aminoisophthalamide as pale yellow crystals.