Sodium Chloride → N-(aminoiminomethyl)-5,6-dihydro-6-oxo-9-methyl-4H-pyrrolo[3,2,1-ij]quinoline-2-carboxamide
Reaction equation
[CH3:1][C:2]1[C:11]2[CH:12]=[C:13]([C:14](OCC)=[O:15])[N:9]3[C:10]=2[C:5]([C:6](=[O:19])[CH2:7][CH2:8]3)=[CH:4][CH:3]=1.Cl.[NH2:21][C:22]([NH2:24])=N.C[O-].[Na+].[Cl-].[Na+].C[N:31](C)C=O>>[NH2:31][N:21]=[CH:22][NH:24][C:14]([C:13]1[N:9]2[C:10]3[C:5]([C:6](=[O:19])[CH2:7][CH2:8]2)=[CH:4][CH:3]=[C:2]([CH3:1])[C:11]=3[CH:12]=1)=[O:15]Participants
Reactant 5
Product 1
Procedure
A mixture of ethyl 5,6-dihydro-9-methyl-6-oxo-4H-pyrrolo[3,2,1-ij]quinoline-2-carboxylate (0.65 g, 2.53 mmol), guanidine hydrochloride (1.21 g, 12.6 mmol), sodium methoxide (0.68 g, 12.6 mmol) and N,N-dimethylformamide (35 ml) was stirred at room temperature for 18 hours. The reaction mixture was poured into a 10% aqueous sodium chloride solution and extracted three times with ethyl acetate, and the extract solution was washed with a 5% aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain crude N-(aminoiminomethyl)-5,6-dihydro-6-oxo-9-methyl-4H-pyrrolo[3,2,1-ij]quinoline-2-carboxamide. This crude product was added to a mixture of aqueous isopropanol and methanesulfonic acid (0.47 g, 4.89 mmol) and dissolved therein by heating, and the resulting solution was cooled to 0° C. The crystals precipitated were collected by filtration and then recrystallized from water to obtain N-(aminoiminomethyl)-5,6-dihydro-9-methyl-6-oxo-4H-pyrrolo[3,2,1-ij]quinoline-2-carboxamide methanesulfonate (0.57 g).
Workup
- extractionextracted three times with ethyl acetate
- washthe extract solution was washed with a 5% aqueous sodium chloride solution
- dry with materialdried over anhydrous magnesium sulfate
- distillationThe solvent was distilled off under reduced pressure
Sources & evidence
- ORD record
- ord-55792cbfe8154692803ece79514111ab
- Source dataset
- uspto-grants-2001_08
- Patent number
- US06271251B1
Reaction notes
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