Sodium Nitrite → HCID 73415363, compound

HRID 478850Notes

Reaction equation

HRID 478850 reaction equation
[N:1]([O-:3])=O.[Na+].[CH:5](=[C:12]1[NH:16][C:15](=[O:17])[CH:14]=[C:13]1[OH:18])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C(O)(=O)C>[CH:5](=[C:12]1[NH:16][C:15](=[O:17])[CH2:14][C:13]1([OH:18])[N:1]=[O:3])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 23668193Sodium NitriteHCID 69721150HCID 69721150, compound

Product 1

HCID 73415363HCID 73415363, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

An aqueous solution of sodium nitrite (0.075 g, 1.1 mmol) was added to an ice-cooled suspension of 2 mmol (0.432 g) 5-benzylidene-4-hydroxy-1,5-dihydro-pyrrol-2-one (prepared by the method of H. Poschenrieder et al (Arch. Pharm. Pharm. Med. Chem. 1998, vol. 331, pp. 389-394) and 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, and the mixture was stirred at room temperature for 30 minutes. The reaction solution was concentrated and orange crystals of 5-benzylidene-4-hydroxy-4-nitroso-1,5-dihydro-pyrrol-2-one were obtained in a yield of 65% by recrystallization from ethanol. The substance decomposes at 205° C.

Workup

  1. temperaturecooled
  2. customprepared by the method of H
  3. concentrationThe reaction solution was concentrated

Sources & evidence

ORD record
ord-1f84814cdd1344cd9887bb364c3bd340
Source dataset
uspto-grants-2003_11
Patent number
US06642267B2

Reaction notes

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