Hydrochloric Acid → 2-chloro-4-[N'-(2-ethoxycarbonyl-1-acetylethylidene)hydrazino]benzoic acid

HRID 1584743Notes

Reaction equation

HRID 1584743 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4](C=[CH:9][C:10]=1Cl)C(O)=O.[ClH:12].[N:13]([O-])=O.[Na+].C([CH:20]([C:27](=[O:29])[CH3:28])[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])(=O)C.[C:30]([O-:33])(=[O:32])[CH3:31].[Na+]>O.C(O)C>[Cl:12][C:4]1[CH:3]=[C:2]([NH:1][N:13]=[C:20]([C:27](=[O:29])[CH3:28])[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:10]=[CH:9][C:31]=1[C:30]([OH:33])=[O:32]

Participants

8

Reactant 5

HCID 313Hydrochloric Acid2×HCID 760923-Amino-4-chlorobenzoic acidHCID 87820Ethyl 3-acetyl-4-oxopentanoateHCID 517045Sodium AcetateHCID 23668193Sodium Nitrite

Product 1

HCID 867532112-chloro-4-[N'-(2-ethoxycarbonyl-1-acetylethylidene)hydrazino]benzoic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent3×

Procedure

To a suspension of 1 gm. (5.8 mmoles) of 3-amino-4-chlorobenzoic acid in 20 ml. of ethanol was added 5 ml. of water and 1 ml. of 12 N hydrochloric acid. The resultant solution was cooled in an ice bath and to the cooled solution was added in small portions 442 mg. (6.4 mmoles) of sodium nitrite in 3 ml. of water. The mixture was allowed to warm to room temperature and after 30 minutes was added to a suspension of 1.19 gm. (6.4 mmole) of ethyl 3-acetyl-4-oxopentanoate, 1.8 gm. of sodium acetate, 20 ml. of ethanol and 5 ml. of water. The reaction mixture turned dark orange. After stirring for one hour, the mixture was acidified with 3N hydrochloric acid and the resultant solids collected by filtration. After drying the material, 2.53 g. was obtained.

Workup

  1. additionTo a suspension of 1 gm
  2. additionwas added in small portions 442 mg
  3. additionwas added to a suspension of 1.19 gm
  4. filtrationthe resultant solids collected by filtration
  5. customAfter drying the material, 2.53 g
  6. customwas obtained

Sources & evidence

ORD record
ord-776a68d945bf41b4b6defb04aceafeba
Source dataset
uspto-grants-1999_08
Patent number
US05935957

Reaction notes

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