N-Ethyl-3-nitro PABA → 3-amino-4-ethylamino-benzoic Acid

HRID 1591969Notes

Reaction equation

HRID 1591969 reaction equation
[CH2:1]([NH:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][C:5]=1[N+:13]([O-])=O)[CH3:2]>C1COCC1.O.[Ni]>[NH2:13][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:4]=1[NH:3][CH2:1][CH3:2])[C:8]([OH:10])=[O:9]

Participants

4

Reactant 1

HCID 3729086N-Ethyl-3-nitro PABA

Product 1

HCID 8544283-amino-4-ethylamino-benzoic Acid

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21881883Oxolane--water (1/1)Solvent

Procedure

A solution of 1.56 g (7.4 mmol) of the title A compound 4-ethylamino-3-nitro-benzoic acid in 60 mL of THF/water (2:1) is hydrogenated at 20 psi over 300 mg of Raney nickel for 18 h. The catalyst is removed by filtration through Celite and the solvent is removed under reduced pressure to give 3-amino-4-ethylamino-benzoic acid as a dark solid. This material is used as such in the next step.

Workup

  1. customThe catalyst is removed by filtration through Celite
  2. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-6d237297cbed410e884e3be43b602fb6
Source dataset
uspto-grants-2007_11
Patent number
US07291635B2

Reaction notes

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