3-Nitro-4-(propylamino)benzoic acid → 3-Amino-4-(propylamino)benzoic acid

HRID 74260Notes

Reaction equation

HRID 74260 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[NH:13][CH2:14][CH2:15][CH3:16])[C:7]([OH:9])=[O:8])([O-])=O.[H][H]>[C].[Pd].O1CCCC1>[NH2:1][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[NH:13][CH2:14][CH2:15][CH3:16])[C:7]([OH:9])=[O:8]

Participants

5

Reactant 2

HCID 117155563-Nitro-4-(propylamino)benzoic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 115864403-Amino-4-(propylamino)benzoic acidYield 80.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a tetrahydrofuran solution (20 mL) of 3-nitro-4-n-propylaminobenzoic acid (see Working Example 82-1) (1.94 g, 10.8 mmol) was added 10% palladium-carbon (200 mg), a hydrogen atmosphere was substituted in the flask, and this was stirred at room temperature for 6 hours. After the reaction was finished, this was filtered through Celite, and the filtrate was concentrated to yield the title compound (1.68 g, quant.).

Workup

  1. filtrationthis was filtered through Celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-a854e5f5d9244b99accc6c643ed3c657
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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