Sodium Carbonate → HCID 12724759, compound

HRID 1742929Notes

Reaction equation

HRID 1742929 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([NH:12][CH3:13])=[C:6]([CH:11]=1)[C:7]([NH:9][NH2:10])=[O:8].[C:14]([O:24]CC)(=[O:23])[CH2:15][C:16]([C:18](OCC)=O)=O.[Na].C(=O)([O-])[O-].[Na+].[Na+]>O>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[N:12]([CH3:13])[C:18]3=[CH:16][C:15]([C:14]([OH:24])=[O:23])=[N:10][N:9]3[C:7](=[O:8])[C:6]=2[CH:11]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 66951Diethyl oxalacetateHCID 5360545SodiumHCID 15224709HCID 15224709, compound

Product 1

HCID 12724759HCID 12724759, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The procedure of Sircar, et al., (J. Med. Chem., 24:735-742 (1981)) was followed. A mixture of 5-amino-2-methylaminobenzoic acid hydrazide (35.05 g, 0.194 mol) and 95% diethyl oxalacetate, sodium salt (47.33 g, 0.214 mol, Aldrich Chemical Co.) in 1 L of water was refluxed for 2 hours. The dark solution was cooled to room temperature and sodium carbonate (22.68 g, 0.214 mol) was added. The solution was refluxed for 1 hour, then allowed to cool to room temperature overnight. A small amount of solid formed. The mixture was filtered through a pad of Celite, the filtrate was cooled and acidified by dropwise addition of 10% hydrochloric acid. At a pH of about 4, a solid formed, the mixture was filtered, and the yellow-green solid was washed with water and vacuum-dried to give 29.65 g (59%) of the title compound, mp 249°-252° C., dec.

Workup

  1. temperaturewas refluxed for 2 hours
  2. temperatureThe solution was refluxed for 1 hour
  3. temperatureto cool to room temperature overnight
  4. customA small amount of solid formed
  5. filtrationThe mixture was filtered through a pad of Celite
  6. temperaturethe filtrate was cooled
  7. additionacidified by dropwise addition of 10% hydrochloric acid
  8. customAt a pH of about 4, a solid formed
  9. filtrationthe mixture was filtered
  10. washthe yellow-green solid was washed with water
  11. customvacuum-dried

Sources & evidence

ORD record
ord-8e68d710e4574049942a9d692be322a8
Source dataset
uspto-grants-1994_08
Patent number
US05342942

Reaction notes

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