Sodium Nitrite → HCID 178517626, compound

HRID 2084422Notes

Reaction equation

HRID 2084422 reaction equation
[N:1]([O-:3])=O.[Na+].[Cl:5][C:6]1[CH:19]=[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[CH:19]=[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 69860834HCID 69860834, compound

Product 1

HCID 178517626HCID 178517626, 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-chlorobenzylidene)-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-chlorobenzylidene)-pyrrolidine-2,3,4-trione 3-oxime was 60%, with a melting point of 176° 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-de74f13c2eb54d11983498d7fa51056c
Source dataset
uspto-grants-2004_04
Patent number
US06716872B2

Reaction notes

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