4-Amino-3,5-dinitrobenzoic acid → HCID 23172110, compound

HRID 852617Notes

Reaction equation

HRID 852617 reaction equation
[NH2:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:14]([O-])=O>COCCOC.C(Cl)(Cl)Cl.[Pd]>[NH2:14][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([N+:11]([O-:13])=[O:12])[C:2]=1[NH2:1])[C:6]([OH:8])=[O:7]

Participants

5

Reactant 1

HCID 2779294-Amino-3,5-dinitrobenzoic acid

Product 1

HCID 23172110HCID 23172110, compoundYield 113.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalyst2×HCID 6212ChloroformSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 4-amino-3,5-dinitrobenzoic acid (10 g, 44 mmol, 1 equiv) in DME (100 ml) and CHCl3 (10 ml) under nitrogen was added 10% palladium on charcoal (50% wet, 1 g, 5% w/w) and the resulting suspension was stirred under an atmosphere of nitrogen (35 psi) for 15 h. 10% Palladium on charcoal (50% wet, 1 g, 5% w/w) was added and the resulting suspension was stirred under an atmosphere of hydrogen (35 psi) for another 15 h. The catalyst was filtered off through a pad of celite and the solution was concentrated in vacuo to give 3,4-diamino-5-nitrobenzoic acid (D244) (9.85 g, 113%) as a red solid which was used in the next step without further purification. [M−H]−=196.1, RT=2.15 min

Workup

  1. stirringthe resulting suspension was stirred under an atmosphere of hydrogen (35 psi) for another 15 h
  2. filtrationThe catalyst was filtered off through a pad of celite
  3. concentrationthe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-6f53151482494c19be0a0546d7d703f0
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

Loading…