Water → 2,3-Diaminobenzoic acid

HRID 380516

Reaction equation

HRID 380516 reaction equation
[N+:1]([C:4]1[C:12]([N+:13]([O-])=O)=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])([O-])=O.Cl[Sn]Cl.O>C(O)(=O)C.Cl>[NH2:1][C:4]1[C:12]([NH2:13])=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7]

Participants

6

Reactant 3

HCID 962WaterHCID 24479Stannous ChlorideHCID 2833272,3-Dinitrobenzoic acid

Product 1

HCID 1980692,3-Diaminobenzoic acidYield 97.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Procedure

To a suspension of 2 g (9.4 mmol) of 2,3-di-nitrobenzoic acid in 20 mL of acetic acid at 0° C. was added a solution of 14.8 g (65 mmol) SnCl2. 2 H2O in 7 mL of concentrated HCl. After stirring for 2 h at rt, the reaction mixture was concentrated. The residue was dissolved in 30 mL of H2O and the pH was adjusted to pH=12-13 with 6N NaOH. The mixture was filtered and the solid was washed with 0.1N HCl. The combined aqueous fractions were concentrated to give 1.4 g of the title compound.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. dissolutionThe residue was dissolved in 30 mL of H2O
  3. filtrationThe mixture was filtered
  4. washthe solid was washed with 0.1N HCl
  5. concentrationThe combined aqueous fractions were concentrated

Sources & evidence

ORD record
ord-894b9a44de43464aad84271e1e113347
Source dataset
uspto-grants-2001_10
Patent number
US06303593B1

Linked notes

Loading…