4-[(2-Ethoxy-2-oxoacetyl)amino]-3-nitrobenzoic acid → HCID 18415566, compound

HRID 990591Notes

Reaction equation

HRID 990591 reaction equation
[C:1]([NH:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][C:10]=1[N+:18]([O-:20])=O)([C:3](OCC)=[O:4])=[O:2]>CN(C)C=O.[Pt]>[C:13]([C:12]1[CH:11]=[C:10]2[C:9]([NH:8][C:1](=[O:2])[C:3](=[O:4])[N:18]2[OH:20])=[CH:17][CH:16]=1)([OH:15])=[O:14]

Participants

4

Reactant 1

HCID 184155634-[(2-Ethoxy-2-oxoacetyl)amino]-3-nitrobenzoic acid

Product 1

HCID 18415566HCID 18415566, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 4-ethoxalylamino-3-nitrobenzoic acid (14.0 g, 49.6 mmol) in 800 ml of N,N-dimethylformamide was hydrogenated at room temperature and atmospheric pressure in the presence of 1.3 g of 5% platinum on carbon for 2.5 h. The catalyst was filtered off and washed with N,N-dimethylformamide. The filtrate was evaporated to dryness and the residue was triturated with 500 ml of water and filtered. The crude product was dissolved in 900 ml of 1M potassium dihydrogen phosphate buffer (pH 7.4), filtered and reprecipitated with 6 M hydrochloric acid to yield 7.7 g (70%) of the title compound. 1H-NMR (DMSO-d6): 7.25 (d, J=9 Hz, 1H, ArH), 7.75 (dd, J=9 Hz, 2 Hz, 1H, ArH), 7.98 (d, J=2 Hz, 1H, ArH), 12.3 (br.s, 1H, exchangeable).

Workup

  1. customwas hydrogenated at room temperature
  2. filtrationThe catalyst was filtered off
  3. washwashed with N,N-dimethylformamide
  4. customThe filtrate was evaporated to dryness
  5. customthe residue was triturated with 500 ml of water
  6. filtrationfiltered
  7. dissolutionThe crude product was dissolved in 900 ml of 1M potassium dihydrogen phosphate buffer (pH 7.4)
  8. filtrationfiltered
  9. customreprecipitated with 6 M hydrochloric acid

Sources & evidence

ORD record
ord-a1c1b482e5d7470e9c600753565c33eb
Source dataset
uspto-grants-2002_10
Patent number
US06461610B1

Reaction notes

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