Sodium Nitrite → HCID 73994020, compound

HRID 2084419Notes

Reaction equation

HRID 2084419 reaction equation
[N:1]([O-:3])=O.[Na+].[OH:5][C:6]1[C:10](=[C:11]([O:18][CH3:19])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[NH:9][C:8](=[O:20])[CH:7]=1>C(O)(=O)C>[CH3:19][O:18][C:11]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[C:10]1[NH:9][C:8](=[O:20])[C:7](=[N:1][OH:3])[C:6]1=[O:5]

Participants

4

Reactant 2

HCID 23668193Sodium NitriteHCID 69861021HCID 69861021, compound

Product 1

HCID 73994020HCID 73994020, 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 4-hydroxy-5-(methoxyphenyl-methylene)-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-(methoxyphenylmethylene)-pyrrolidine-2,3,4-trione 3-oxime was 60%, with a melting point of 174° 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-af0caab2b19d4ca7b1d812806fbd7a14
Source dataset
uspto-grants-2004_04
Patent number
US06716872B2

Reaction notes

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