Methanol → 5,5-Dimethyl-1-(6-hydroxyquinoline-4-ylmethyl)-3-(4-trifluoromethoxyphenyl)imidazolidine-2,4-dione

HRID 899968Notes

Reaction equation

HRID 899968 reaction equation
B(Br)(Br)Br.[CH3:5][C:6]1([CH3:37])[N:10]([CH2:11][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([O:22]C)[CH:20]=3)[N:15]=[CH:14][CH:13]=2)[C:9](=[O:24])[N:8]([C:25]2[CH:30]=[CH:29][C:28]([O:31][C:32]([F:35])([F:34])[F:33])=[CH:27][CH:26]=2)[C:7]1=[O:36].CO.C([O-])(O)=O.[Na+]>C(Cl)Cl.O>[CH3:5][C:6]1([CH3:37])[N:10]([CH2:11][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([OH:22])[CH:20]=3)[N:15]=[CH:14][CH:13]=2)[C:9](=[O:24])[N:8]([C:25]2[CH:26]=[CH:27][C:28]([O:31][C:32]([F:34])([F:35])[F:33])=[CH:29][CH:30]=2)[C:7]1=[O:36]

Participants

7

Reactant 4

HCID 887MethanolHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 596942685,5-Dimethyl-1-(6-methoxyquinolin-4-ylmethyl)-3-(4-trifluoromethoxyphenyl)imidazolidine-2,4-dione

Product 1

HCID 596942575,5-Dimethyl-1-(6-hydroxyquinoline-4-ylmethyl)-3-(4-trifluoromethoxyphenyl)imidazolidine-2,4-dioneYield 67.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Conditions

Temperature
20 °C

Procedure

6 ml of a 1M solution of boron tribromide in CH2Cl2 are added to a solution of 0.26 g of 5,5-dimethyl-1-(6-methoxyquinolin-4-ylmethyl)-3-(4-trifluoromethoxyphenyl)imidazolidine-2,4-dione in 40 ml of dichloromethane, under an inert atmosphere of argon at a temperature in the region of 0° C. The reaction medium is stirred at a temperature in the region of 20° C. for 16 hours. 5 ml of methanol are added dropwise. After stirring for 30 minutes at this temperature, 50 ml of water, 30 ml of CH2Cl2 and 10 ml of saturated NaHCO3 are added. After separation of the phases by settling, the organic phase is dried over sodium sulfate, filtered and then concentrated under reduced pressure. The beige-colored foam obtained is purified by flash chromatography (SiO2, EtOAc as eluent, Ar). The fractions containing the product are concentrated under reduced pressure. 0.17 g of 5,5-dimethyl-1-(6-hydroxyquinoline-4-ylmethyl)-3-(4-trifluoromethoxyphenyl)imidazolidine-2,4-dione is thus obtained, the characteristics of which product are as follows:

Workup

  1. additionare added
  2. customAfter separation of the phases
  3. dry with materialthe organic phase is dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe beige-colored foam obtained
  7. customis purified by flash chromatography (SiO2, EtOAc as eluent, Ar)
  8. additionThe fractions containing the product
  9. concentrationare concentrated under reduced pressure

Sources & evidence

ORD record
ord-66d819150265469bb71e9a2a7d649ebc
Source dataset
uspto-grants-2008_04
Patent number
US07354933B2

Reaction notes

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