Sodium Bicarbonate → 4-Aminoisophthalamide

HRID 1356651Notes

Reaction equation

HRID 1356651 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

HCID 516892Sodium BicarbonateHCID 14931587HCID 14931587, compound

Product 1

HCID 149353654-AminoisophthalamideYield 50%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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.

Workup

  1. temperatureAfter cooling
  2. customformed
  3. customwere removed by filtration
  4. extractionThe filtrate was extracted with ethyl acetate
  5. dry with materialthe extract was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ee60b76908ce4f429a5f24ed55979f8c
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Reaction notes

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