Dimethylamine → 7-Chloro-3-methyl-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid dimethylamide
Reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:22])[C:7]([CH3:21])=[C:8]([C:18](O)=[O:19])[N:9]2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)[N:32]1[CH2:36]CC[CH2:33]1.C(N(CC)C(C)C)(C)C.CNC>CN(C=O)C>[CH3:33][N:32]([CH3:36])[C:18]([C:8]1[N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:10]2[C:5]([C:6](=[O:22])[C:7]=1[CH3:21])=[CH:4][CH:3]=[C:2]([Cl:1])[CH:11]=2)=[O:19]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
In a 50 mL round bottom flask, 7-chloro-3-methyl-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid (0.5 g, 1.60 mmol), bromo-tris-pyrrolidino-phosphonium hexafluorophosphate (PyBrOP, 1.11 g, 2.39 mmol) and N,N-diisopropylethylamine (1.11 mL, 6.37 mmol) were added to anhydrous DMF (5.0 mL). The mixture was stirred at room temperature for 30 min. Dimethylamine (2M in THF, 1.6 mL, 3.2 mmol) was added and the reaction mixture was stirred at room temperature for 48 hr. The mixture was concentrated to dryness and the crude was purified by flash chromatography using 3:2 hexane-ethyl acetate to afford 7-chloro-3-methyl-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid dimethylamide (600 mg, >100% yield). MS calcd for C19H17ClN2O2 [(M+H)+] 341, obsd 341.
Workup
- stirringthe reaction mixture was stirred at room temperature for 48 hr
- concentrationThe mixture was concentrated to dryness
- customthe crude was purified by flash chromatography
Sources & evidence
- ORD record
- ord-83ac3126b6184a8aa7cf7c031edb12d5
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08501732B2
Reaction notes
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