Methyl chloroformate → Flometoquin

HRID 384836Notes

Reaction equation

HRID 384836 reaction equation
[CH2:1]([C:3]1[NH:4][C:5]2[C:10]([C:11](=[O:14])[C:12]=1[CH3:13])=[CH:9][C:8]([O:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][C:23]([F:26])([F:25])[F:24])=[CH:18][CH:17]=1)=[C:7]([CH3:27])[CH:6]=2)[CH3:2].[H-].[Na+].Cl[C:31]([O:33][CH3:34])=[O:32]>CN(C)C=O>[C:31](=[O:32])([O:33][CH3:34])[O:14][C:11]1[C:10]2[C:5](=[CH:6][C:7]([CH3:27])=[C:8]([O:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][C:23]([F:24])([F:25])[F:26])=[CH:18][CH:17]=3)[CH:9]=2)[N:4]=[C:3]([CH2:1][CH3:2])[C:12]=1[CH3:13]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 24758Sodium hydrideHCID 67119408HCID 67119408, compound

Product 1

HCID 67119441FlometoquinYield 91.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
15 °C

Procedure

Dimethylformamide (980 ml) and 98 g of 2-ethyl-3,7-dimethyl-6-(4-(trifluoromethoxy)phenoxy)quinolin-4(1H)-one were charged into a 2000-ml glass flask equipped with a stirring device, a thermometer, a reflux condenser, and a calcium chloride tube under a nitrogen atmosphere, and the temperature of the contents of the flask was cooled to 15° C. A 55% sodium hydride (18.2 g) was added thereto, and a reaction was allowed to proceed at 15 to 20° C. for one hr. Methyl chloroformate (32.1 g) was added dropwise into the reaction solution, and a reaction was allowed to proceed at room temperature for one hr. The reaction mixture was poured into 5 L of ice-water contained in the a 10-L plastic container, and the mixture was stirred at room temperature for two hr. The precipitated solid was collected by filtration through a suction filter and was washed with water and n-hexane. The solid was dried under the reduced pressure to give 2-ethyl-3,7-dimethyl-6-(4-(trifluoromethoxy)phenoxy)quinolin-4-yl methyl carbonate (103.3 g, yield: 91.4%). The results of 1H-NMR analysis showed that the compound thus obtained was No. 120 described in a brochure of International Publication No. 2006/013896.

Workup

  1. customequipped with a stirring device
  2. waitto proceed at room temperature for one hr
  3. filtrationThe precipitated solid was collected by filtration through a suction
  4. filtrationfilter
  5. washwas washed with water and n-hexane
  6. customThe solid was dried under the reduced pressure

Sources & evidence

ORD record
ord-2d487c766ad94fd7baab264ab8b87218
Source dataset
uspto-grants-2013_02
Patent number
US08367833B2

Reaction notes

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