3-Nitro-1-naphthoic acid → 3-aminonaphthalene-1-carboxylic Acid

HRID 378125Notes

Reaction equation

HRID 378125 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:14]([OH:16])=[O:15])[C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([C:14]([OH:16])=[O:15])[C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2

Participants

4

Reactant 1

HCID 2307723-Nitro-1-naphthoic acid

Product 1

HCID 2721383-aminonaphthalene-1-carboxylic AcidYield 95.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3-Nitro-1-naphthoic acid (1.77 g, 0.008 mole) was dissolved in a minimum of warm MeOH. 10% Pd/C (300 mg) was added and the reaction shaken on a Parr shaker under 50 psi H2 for 5 hours. The catalyst was filtered through celite and the solvent was removed under vacuum. The residue was dried to yield 3-amino-1-naphthoic acid (1.43 g) as a pink colored solid.

Workup

  1. filtrationThe catalyst was filtered through celite
  2. customthe solvent was removed under vacuum
  3. customThe residue was dried

Sources & evidence

ORD record
ord-16a41ebe79e546068a666422bbfa5f8e
Source dataset
uspto-grants-2000_02
Patent number
US06028223

Reaction notes

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