Sodium Nitrite → HCID 178517652, compound

HRID 2084425Notes

Reaction equation

HRID 2084425 reaction equation
[N:1]([O-:3])=O.[Na+].[Cl:5][C:6]1[CH:19]=[C:18]([Cl:20])[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[CH:19]=[C:18]([Cl:20])[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 69861410HCID 69861410, compound

Product 1

HCID 178517652HCID 178517652, 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-(2,4-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-bd68de2b1e4f48a09b6f1d30298d121f
Source dataset
uspto-grants-2004_04
Patent number
US06716872B2

Reaction notes

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