Ammonia → HCID 73415357, compound

HRID 478858Notes

Reaction equation

HRID 478858 reaction equation
[N+:1](=C)=[N-].[CH:4](=[C:11]1[NH:15][C:14](=[O:16])[C:13]([N+:17]([O-:19])=[O:18])=[C:12]1O)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.N>CCOCC.CO>[NH2:1][C:12]1[C:11](=[CH:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[NH:15][C:14](=[O:16])[C:13]=1[N+:17]([O-:19])=[O:18]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 9550DiazomethaneHCID 76170707HCID 76170707, compound

Product 1

HCID 73415357HCID 73415357, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

An excess of diazomethane in ether is added to a suspension of 0.46 g (2 mmol) benzylidene-4-hydroxy-3-nitro-3-pyrrolin-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 20 ml methanol. When the evolution of nitrogen has subsided, the solvent is stripped off, the residue is dissolved in methanol and the solution is heated under reflux with an excess of ammonia solution for five minutes, whereupon yellow crystals precipitate out, which are filtered off with suction and washed with methanol. 4-Amino-5-benzylidene-3-nitro-1,5-dihydropyrrol-2-one obtained with a melting point of >260° C. in a yield of 75%.

Workup

  1. customprepared by the method of H
  2. temperaturethe solution is heated
  3. customwhereupon yellow crystals precipitate out
  4. filtrationwhich are filtered off with suction
  5. washwashed with methanol

Sources & evidence

ORD record
ord-77c7d68293df4749bd111ebd24c70210
Source dataset
uspto-grants-2003_11
Patent number
US06642267B2

Reaction notes

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