Benzylamine → HCID 73415360, compound

HRID 478856Notes

Reaction equation

HRID 478856 reaction equation
[N+](=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.[CH2:21]([NH2:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CCOCC.CO>[CH2:21]([NH:28][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])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 7504BenzylamineHCID 9550DiazomethaneHCID 76170707HCID 76170707, compound

Product 1

HCID 73415360HCID 73415360, compoundYield 60%

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 benzylamine for five minutes, whereupon yellow crystals precipitate out, which are filtered off with suction and washed with methanol. 4-Benzylamino-5-benzylidene-3-nitro-1,5-dihydropyrrol-2-one was obtained with a melting point of 218° C. in a yield of 60%.

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-2326ea067f5543c5a35614885a8ac467
Source dataset
uspto-grants-2003_11
Patent number
US06642267B2

Reaction notes

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