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

HRID 399415

Reaktionsgleichung

Reaktionsgleichung von HRID 399415
[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]

Komponenten

8

Edukt 5

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittel2×HCID 962WaterLösungsmittel3×

Versuchsvorschrift

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 3 N hydrochloric acid and the resultant solids collected by filtration. After drying the material, 2.53 g. was obtained.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-cfd35857535145c487ef71836db4a77d
Quelldatensatz
uspto-grants-1998_10
Patentnummer
US05821243

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