Diazomethane → HCID 85039982, compound

HRID 478851Notes

Reaction equation

HRID 478851 reaction equation
[N+](=[CH2:3])=[N-].[CH:4](=[C:11]1[NH:15][C:14](=[O:16])[C:13]([N:17]=[O:18])=[C:12]1[OH:19])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>CO>[CH:4](=[C:11]1[NH:15][C:14](=[O:16])[C:13]([N:17]=[O:18])=[C:12]1[O:19][CH3:3])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 136343242HCID 136343242, compound

Product 1

HCID 85039982HCID 85039982, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

An excess of an ethereal diazomethane solution was added to a suspension of 5-benzylidene-4-hydroxy-3-nitroso-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 methanol. After the vigorous evolution of nitrogen has subsided, the reaction solution is concentrated in vacuo and the residue thus obtained is recrystallized from methanol. Red crystals of 5-benzylidene-4-methoxy-3-nitroso-1,5-dihydropyrrol-2-one with a melting point of 172° C. were obtained in a yield of 90%.

Workup

  1. customprepared by the method of H
  2. concentrationthe reaction solution is concentrated in vacuo
  3. customthe residue thus obtained
  4. customis recrystallized from methanol

Sources & evidence

ORD record
ord-441bb32c477744f6af6f605022102d98
Source dataset
uspto-grants-2003_11
Patent number
US06642267B2

Reaction notes

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