Sodium Nitrite → HCID 178517642, compound

HRID 2084424Notes

Reaction equation

HRID 2084424 reaction equation
[N:1]([O-:3])=O.[Na+].[Cl:5][C:6]1[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:7]=1[CH:8]=[C:9]1[NH:13][C:12](=[O:14])[CH:11]=[C:10]1[OH:15]>C(O)(=O)C>[Cl:5][C:6]1[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:7]=1[CH:8]=[C:9]1[NH:13][C:12](=[O:14])[C:11](=[N:1][OH:3])[C:10]1=[O:15]

Participants

4

Reactant 2

HCID 23668193Sodium NitriteHCID 69861046HCID 69861046, compound

Product 1

HCID 178517642HCID 178517642, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

An aqueous solution of 1.1 mmol (0.075 g) sodium nitrite was added dropwise to an ice-cooled solution of 2 mmol 5-(2,3-dichlorobenzylidene)-4-hydroxy-1,5-dihydropyrrol-2-one (prepared in accordance with H. Poschenrieder et al (Arch. Pharm. Pharm. Med. Chem. 1998, 331, 389-394) and H.-D. Stachel et al (J. Heterocycl. Chem. 1980, vol. 17, pp. 1195-1199) and Liebigs Ann. Chem. 1985, pp. 1692-1696)) in 5 ml glacial acetic acid, while stirring. The resulting solution was then stirred at room temperature for 30 minutes and concentrated in vacuo. The residue is purified by recrystallization from ethanol. The yield of 5-(2,4-dichlorobenzylidene)-pyrrolidine-2,3,4-trione 3-oxime was 55%, with a melting point of 180° C.

Workup

  1. customprepared in accordance with H
  2. concentrationconcentrated in vacuo
  3. customThe residue is purified by recrystallization from ethanol

Sources & evidence

ORD record
ord-96fea8fbe9984c1e82eab0be3171ed1e
Source dataset
uspto-grants-2004_04
Patent number
US06716872B2

Reaction notes

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