Dimethylformamide → Methyl 7-bromo-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylate

HRID 1801988Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[O:11])O[C:8](=[O:12])[N:7]([CH3:13])[C:6]=2[CH:14]=1.[H-].[Na+].CN(C=O)C.BrC1C=C[C:26]2[C:31](=[O:32])[O:30][C:29](=O)NC=2C=1.IC>O>[Br:1][C:2]1[CH:14]=[C:6]2[C:5]([C:10]([OH:11])=[C:26]([C:31]([O:30][CH3:29])=[O:32])[C:8](=[O:12])[N:7]2[CH3:13])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

7-Bromo-1-methyl-1H-benzo[d][1,3]oxazine-2,4-dione. Sodium hydride (0.47 g, 12 mmol) was added to a 3 neck 250 mL round bottom flask under nitrogen and then washed with hexanes. Once the hexanes were decanted, DMF (20.0 mL, 11 mmol) was added. The resulting mixture was cooled to 0° C. using an ice-water bath, and then 7-bromo-1H-benzo[d][1,3]oxazine-2,4-dione (2.7 g, 11 mmol) was added in one batch. After stirring at room temperature for 1 hour, iodomethane (0.70 mL, 11 mmol) was added dropwise to the yellow solution, and the reaction mixture was stirred for 16 hours. Water (50 mL) was added, and the resulting precipitate that formed was collected via filtration. The solid was washed with additional water (100 mL), followed by ether (100 mL). Drying in a vacuum oven overnight at 50° C. provided the title compound as an off-white solid (2.1 g, 74% yield).

Workup

washwashed with hexanes
customOnce the hexanes were decanted
stirringthe reaction mixture was stirred for 16 hours
customthe resulting precipitate that formed
filtrationwas collected via filtration
washThe solid was washed with additional water (100 mL)
customDrying in a vacuum oven overnight at 50° C.

Sources & evidence

ORD record: ord-23475fec9a24441593730a7789b2e887
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349868B2

Reaction notes

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