Reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([OH:13])=O)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C(Cl)=O.CCN(C(C)C)C(C)C.Cl.[CH3:30][O:31][NH:32][CH3:33]>CN(C=O)C.C(Cl)Cl>[CH3:30][O:31][N:32]([CH3:33])[C:11]([C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[N:1]=[CH:2][CH:3]=[CH:4]2)=[O:13]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
A 250 mL RB flask was charged with quinoline-6-carboxylic acid (5.00 g, 28.9 mmol), DCM (100 ml, 1554 mmol), oxalyl chloride (3.79 ml, 43.3 mmol), and a few drops of DMF and stirred at RT for 2 hours, then concentrated. The residue was taken up in DCM (100 ml, 1554 mmol), cooled to 0° C., then Hunig's Base (17.7 ml, 101 mmol) and N-methoxymethanamine hydrochloride (2.96 g, 30.3 mmol) were added slowly. The mixture was stirred at room temperature for 16 hours (91463-3-1). The mixture was diluted with DCM (200 mL), then washed with water (250 mL), sat. NaHCO3 (250 mL), and brine (250 mL). The organic layer was dried with MgSO4, filtered, and concentrated to give a brown oil, which was purified by MPLC eluting with 2-6% MeOH/DCM to give N-methoxy-N-methylquinoline-6-carboxamide (5.943 g, 95.2% yield) as a brown oil.
Workup
- concentrationconcentrated
- temperaturecooled to 0° C.
- washwashed with water (250 mL), sat. NaHCO3 (250 mL), and brine (250 mL)
- dry with materialThe organic layer was dried with MgSO4
- filtrationfiltered
- concentrationconcentrated
- customto give a brown oil, which
- customwas purified by MPLC
- washeluting with 2-6% MeOH/DCM
Sources & evidence
- ORD record
- ord-1c22e723dddd4c25b16eeb5f4c0677ad
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08524900B2
Linked notes
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