Tetrahydrofuran → 2,3-Diaminobenzoic acid

HRID 1393361Notes

Reaction equation

HRID 1393361 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].O1CCCC1>CO.[C].[Pd]>[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

5

Reactant 2

HCID 8028TetrahydrofuranHCID 2196332-Amino-3-nitrobenzoic acid

Product 1

HCID 1980692,3-Diaminobenzoic acidYield 107%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

10% Palladium carbon (water content 51.7%, 250 mg) was added to a solution of methyl ester of 2-amino-3-nitrobenzoic acid (980 mg, 5.00 mmol) in methanol (20 ml)-tetrahydrofuran (10 ml) and the mixture was stirred under hydrogen atmosphere at room temperature for 3 hrs. The catalyst was removed by filtration and washed with tetrahydrofuran. The filtrate and washings were combined and the solvent was distilled off under reduced pressure to give methyl ester of 2,3-diaminobenzoic acid (814 mg, 98%) as a yellowish green solid.

Workup

  1. customThe catalyst was removed by filtration
  2. washwashed with tetrahydrofuran
  3. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-a2a0e3090d824885a1c3a591fd8037fe
Source dataset
uspto-grants-2008_03
Patent number
US07345068B2

Reaction notes

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