3-Nitro-5-(2-oxopyrrolidin-1-yl)benzoic acid → 3-Amino-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid

HRID 852520Notes

Reaction equation

HRID 852520 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([N:13]2[CH2:17][CH2:16][CH2:15][C:14]2=[O:18])[CH:12]=1)[C:7]([OH:9])=[O:8])([O-])=O>CO.O.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([N:13]2[CH2:17][CH2:16][CH2:15][C:14]2=[O:18])[CH:12]=1)[C:7]([OH:9])=[O:8]

Participants

4

Reactant 1

HCID 222530233-Nitro-5-(2-oxopyrrolidin-1-yl)benzoic acid

Product 1

HCID 222529903-Amino-5-(2-oxo-pyrrolidin-1-yl)-benzoic acidYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 22242641Methanol--water (1/1)Solvent

Procedure

To a solution of 3-nitro-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid (A27) (4 g, 16 mmol, 1 equiv) in MeOH/H2O (9:1, 40 ml) was added 10% palladium on charcoal (50% wet, 800 mg, 0.1 equiv w/w). The resulting mixture was stirred for 6 h at atmospheric pressure under an atmosphere of hydrogen. The catalyst was removed by filtration through a pad of celite and the solvent was removed in vacuo. The residue was dried at 60° C. under vacuum for 16 h to give 3-amino-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid (D6) (3.34 g, 15.2 mmol, 95%) as a pale brown solid. [M−H]−=218.8, RT=1.86 min

Workup

  1. customThe catalyst was removed by filtration through a pad of celite
  2. customthe solvent was removed in vacuo
  3. customThe residue was dried at 60° C. under vacuum for 16 h

Sources & evidence

ORD record
ord-292d459d7c1149f3bde63c9cf17ace63
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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