Potassium Acetate → 2,3-Diaminobenzoic acid methyl ester

HRID 622105Notes

Reaction equation

HRID 622105 reaction equation
C([O-])(=O)C.[K+].Cl[C:7]1[CH:16]=[C:11]([C:12]([O:14][CH3:15])=[O:13])[C:10]([NH2:17])=[C:9]([N+:18]([O-])=O)[CH:8]=1>[C].[Pd].CO>[NH2:17][C:10]1[C:9]([NH2:18])=[CH:8][CH:7]=[CH:16][C:11]=1[C:12]([O:14][CH3:15])=[O:13]

Participants

5

Reactant 2

HCID 517044Potassium AcetateHCID 615489Methyl 2-amino-5-chloro-3-nitrobenzoate

Product 1

HCID 5718252,3-Diaminobenzoic acid methyl ester

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A mixture of 5 g 5% palladium-carbon, 2.8 liters of methanol, 59 g of potassium acetate (anhydride), and 138.4 g methyl 5-chloro-3-nitroanthranilate was subjected to hydrogen absorption with stirring and cooling with a water bath. When the hydrogen absorption was completed, the reaction mixture was filtered, and the filtrate was concentrated in vacuo. To the residue were added ice and 1 lit mixture of n-hexane:ethyl acetate (6:4) and separated. The organic solvent layer was washed with saturated sodium bicarbonate solution, then washed with saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated in vacuo to give dark brown crystals, m.p. 59°-61° C.

Workup

  1. customwas subjected to hydrogen absorption
  2. temperaturecooling with a water bath
  3. customWhen the hydrogen absorption
  4. filtrationthe reaction mixture was filtered
  5. concentrationthe filtrate was concentrated in vacuo
  6. additionTo the residue were added ice and 1
  7. additionmixture of n-hexane:ethyl acetate (6:4)
  8. customseparated
  9. washThe organic solvent layer was washed with saturated sodium bicarbonate solution
  10. washwashed with saturated sodium chloride solution
  11. dry with materialdried with anhydrous magnesium sulfate
  12. concentrationconcentrated in vacuo
  13. customto give dark brown crystals, m.p. 59°-61° C.

Sources & evidence

ORD record
ord-14afc9aff70a46ccbfd53437f42d9010
Source dataset
uspto-grants-1988_09
Patent number
US04769384

Reaction notes

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