Sodium Hydroxide → 2,3-Diaminobenzoic acid

HRID 541059Notes

Reaction equation

HRID 541059 reaction equation
[NH2:1][C:2]1[C:10]([N+:11]([O-])=O)=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[OH-].[Na+].O.NN>[Ni].CO>[NH2:1][C:2]1[C:10]([NH2:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 2196332-Amino-3-nitrobenzoic acid2×

Product 1

HCID 1980692,3-Diaminobenzoic acid

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent3×

Conditions

Temperature
65 °C

Procedure

3 g of the above mentioned 2-amino-3-nitrobenzoic acid is added into 30 ml of methanol, 20% sodium hydroxide aqueous solution with the same molar as 2-amino-3-nitrobenzoic acid is dropped into the above methanol solution till dissolve completely. 0.2 g of Raney nickel at the moment is added in to the methanol solution, and to heat it to 65° C. and reflux it at the temperature; and then drop 80 g/g % hydrazine hydrate (about 1.5 equivalent weight×1.1) till the yellow disappears completely. Hot Raney nickel is filtered; and then heat and concentrate the mother liquid and acidize it with the concentrated chlorhydric acid to produce 2.3 g of red 2,3-diaminobenzoic acid; afterwards isolate and purify the crude product of red 2,3-diaminobenzoic acid by column chromatography.

Workup

  1. dissolutiontill dissolve completely
  2. temperaturereflux it at the temperature
  3. filtrationHot Raney nickel is filtered
  4. temperatureand then heat
  5. concentrationconcentrate the mother liquid

Sources & evidence

ORD record
ord-089f41f296394e929af351ab212713f0
Source dataset
uspto-grants-2014_10
Patent number
US08871946B2

Reaction notes

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