Methylamine → HCID 73415362, compound

HRID 478857Notes

Reaction equation

HRID 478857 reaction equation
[N+:1](=[CH2:3])=[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.CN>CCOCC.CO>[CH:4](=[C:11]1[NH:15][C:14](=[O:16])[C:13]([N+:17]([O-:19])=[O:18])=[C:12]1[NH:1][CH3:3])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 6329MethylamineHCID 9550DiazomethaneHCID 76170707HCID 76170707, compound

Product 1

HCID 73415362HCID 73415362, compoundYield 45%

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 methylamine solution for five minutes, whereupon yellow crystals precipitate out, which are filtered off with suction and washed with methanol. 5-Benzylidene-4-methylamino-3-nitro-1,5-dihydropyrrol-2-one was obtained with a melting point of 238° C. in a yield of 45%.

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-206b85f73eea4259aa819ffc07c32790
Source dataset
uspto-grants-2003_11
Patent number
US06642267B2

Reaction notes

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