Formamide → HCID 23030616, compound
Reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[CH:10][CH:9]=[CH:8]2)=[O:4].S([O-])([O-])(=O)=O.OO.C(=O)([O-])[O-].[K+].[K+].[CH:28]([NH2:30])=[O:29]>CO.C(Cl)(Cl)Cl.O>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[C:10]([C:28]([NH2:30])=[O:29])[CH:9]=[CH:8]2)=[O:4]Participants
Conditions
- Temperature
- 80 °C
Procedure
4.0 g of 6-quinolinecarboxylic acid were suspended in 30 ml of MeOH, 2.0 ml of conc. sulfate was added under ice cooling, and the mixture was stirred at 70° C. for 22 hours. The reaction solution was concentrated under reduced pressure, and the residue was mixed with water and neutralized with potassium carbonate. The thus-precipitated solid was filtered and dried to obtain 4.28 g of 6-quinolinecarboxylic acid methyl ester. 0.5 g of the obtained ester body was dissolved in 5 ml of formamide, 0.15 ml of conc. sulfate, 0.05 g of ferrous sulfate hepta-hydrate, and 0.4 ml of 31% hydrogen peroxide were sequentially added thereto, and the mixture was stirred at 80° C. for 50 minutes. The reaction solution was mixed with water and alkalinized with potassium carbonate. 10% MeOH-chloroform was added, and insoluble matter was filtered using celite. The obtained filtrate was separated, the obtained organic layer was dried over anhydrous sodium sulfate and concentrated, and the obtained residue was washed with EtOH to obtain 0.15 g of 6-methoxycarbonyl-2-quinolinecarboxamide.
Workup
- filtrationinsoluble matter was filtered
- customThe obtained filtrate was separated
- dry with materialthe obtained organic layer was dried over anhydrous sodium sulfate
- concentrationconcentrated
- washthe obtained residue was washed with EtOH
Sources & evidence
- ORD record
- ord-635fb412a9954f64a2d7e2fdc4954abc
- Source dataset
- uspto-grants-2009_12
- Patent number
- US07638536B2
Reaction notes
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