Sodium Chloride → Methyl 4-chloro-2-oxo-1,2-dihydroquinoline-3-carboxylate
Reaction equation
[CH3:1][C:2](C)([C:6]([O-:8])=[O:7])[C:3]([O-:5])=O.[H-].[Na+].[C:12]12[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=1)[NH:17]C(=O)OC2=O.[C:24](Cl)(=O)C(Cl)=O.[Na+].[Cl-:31]>CN(C=O)C>[Cl:31][C:1]1[C:19]2[C:18](=[CH:12][CH:22]=[CH:21][CH:20]=2)[NH:17][C:3](=[O:5])[C:2]=1[C:6]([O:8][CH3:24])=[O:7]Participants
Procedure
Dimethylmalonate (2.2 mL, 19.2 mmol) was added slowly to a suspension of 60% sodium hydride in mineral oil (0.81 g, 20.3 mmol) in anhydrous DMF (100 mL) at −10° C. under nitrogen. After stirring at room temperature for 30 minutes, isatoic anhydride (3.0 g, 18.4 mmol) was added, and the reaction mixture was heated at 115° C. for 2.5 hours. The reaction was then cooled to −40° C. and oxalyl chloride (6 mL, 68.8 mmol) was slowly added. The reaction was stirred at room temperature for 20 minutes, and was then poured into 1200 mL of 10% NaCl at 0° C. The resultant precipitate was collected by filtration to give crude methyl 4-chloro-2-oxo-1,2-dihydroquinoline-3-carboxylate (1.40 g, 32%), which was used without further purification. 1H NMR (400 MHz, DMSO-d6) δ3.87 (s, 3H), 7.39 (m, 2H), 7.70 (m, 1H), 7.92 (d, J=8.4 Hz, 1H), 12.49 (s, 1H). MS 238 (MH+).
Workup
- temperaturethe reaction mixture was heated at 115° C. for 2.5 hours
- temperatureThe reaction was then cooled to −40° C.
- stirringThe reaction was stirred at room temperature for 20 minutes
- filtrationThe resultant precipitate was collected by filtration
Sources & evidence
- ORD record
- ord-85363b31e80d42fbaf48e51c488f8842
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08541421B2
Reaction notes
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