Sodium Bicarbonate → 3-Amino-4-(aminocarbonyl)benzoic acid

HRID 906164Notes

Reaction equation

HRID 906164 reaction equation
[NH2:1][C:2]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][C:5]=1[N+:13]([O-])=O)=[O:3].C(=O)(O)[O-].[Na+]>O.[Pd]>[NH2:13][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:4]=1[C:2]([NH2:1])=[O:3])[C:8]([OH:10])=[O:9]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 70164254-Carbamoyl-3-nitrobenzoic acid

Product 1

HCID 541834253-Amino-4-(aminocarbonyl)benzoic acidYield 99.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

4-(aminocarbonyl)-3-nitrobenzoic acid (2.00 g, 9.52 mmol) was suspended in water (50 ml) and sodium bicarbonate (0.80 g, 9.52 mmol) was added. The resulting solution was hydrogenated in the presence of 10% palladium on carbon (300 mg) at 30 psi for 16 hours. The mixture was then filtered through Celite. The filtrate was acidified by addition of concentrated hydrochloric acid and the resulting solid was collected by filtration and dried in vacuo to afford 3-amino-4-(aminocarbonyl)benzoic acid (1.70 g, 99% yield). MS (EI) for C8H8N2O3: 179 (M−H).

Workup

  1. filtrationThe mixture was then filtered through Celite
  2. additionThe filtrate was acidified by addition of concentrated hydrochloric acid
  3. filtrationthe resulting solid was collected by filtration
  4. customdried in vacuo

Sources & evidence

ORD record
ord-dcd90720c9454c4696a67b88e977997d
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

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