Hydrochloric Acid → HCID 178488821, compound

HRID 443821Notes

Reaction equation

HRID 443821 reaction equation
[NH2:1][C:2]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([NH:6][NH2:7])=[O:5].[C:14](OCC)(=O)[CH2:15][C:16]([C:18]([O:20]CC)=[O:19])=O.[Na].C(=O)([O-])[O-].[Na+].[Na+].Cl>O>[CH3:13][O:12][C:11]1[C:2]2[NH:1][C:14]3=[CH:15][C:16]([C:18]([OH:20])=[O:19])=[N:7][N:6]3[C:4](=[O:5])[C:3]=2[CH:8]=[CH:9][CH:10]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 66951Diethyl oxalacetateHCID 5360545SodiumHCID 12724734HCID 12724734, compound

Product 1

HCID 178488821HCID 178488821, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-amino-3-methoxybenzoic acid hydrazide (23,6 g; 0.13 mole) and 90% diethyl oxalacetate, sodium salt (32.7 g; 0.14 mole) in water (400 ml) is heated under reflux for 1.5 hrs. To the resulting yellow solution is added sodium carbonate (14.8 g; 0.14 mole) and the solution is refluxed for an additional hour. The cooled reaction mixture is cautiously treated with conc. HCl (0.28 mole) and the precipitated solid is filtered off, washed with water and recrystallized from methanol (1500 ml). Yield 5.8 g; mp 271°-272° C. (d).

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 1.5 hrs
  3. temperaturethe solution is refluxed for an additional hour
  4. customThe cooled reaction mixture
  5. filtrationthe precipitated solid is filtered off
  6. washwashed with water
  7. customrecrystallized from methanol (1500 ml)

Sources & evidence

ORD record
ord-c137a69f475b45a5b15204038cf59cfc
Source dataset
uspto-grants-1981_04
Patent number
US04261996

Reaction notes

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