1,3-Dibromo-5,5-dimethylhydantoin → 6-Quinolinecarboxylic acid, 3-bromo-, methyl ester

HRID 2080143Notes

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].O1CCCC1.[Br:20]N1C(C)(C)C(=O)N(Br)C1=O.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.O>[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][C:9]([Br:20])=[CH:8]2)=[O:4]

Participants

Conditions

Temperature: 50 °C

Procedure

To a mixture of quinoline-6-carboxylic acid methyl ester (0.50 g, 2.7 mmol) and tetrahydrofuran (10 mL) was added 1,3-dibromo-5,5-dimethyl hydantoin (0.76 g, 2.7 mmol) on an ice bath, and the solution was stirred at 50° C. for 4 hours. Water, an aqueous solution of saturated sodium bicarbonate and ethyl acetate were added to the reaction solution, which was then partitioned, the organic layer was washed with brine, the solvent was then evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1), and the title compound (69 mg, 0.26 mmol, 10%) was obtained as a white solid.

Workup

customwas then partitioned
washthe organic layer was washed with brine
customthe solvent was then evaporated in vacuo
customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record: ord-c7131c5e0c214970ad838c576bd3682a
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07932272B2

Reaction notes

Loading…