Methyl chloroformate → Flometoquin

HRID 2273844Notes

Reaction equation

HRID 2273844 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]>CC(N(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 31374DimethylacetamideSolvent

Conditions

Temperature
15 °C

Procedure

Dimethyl acetamide (980 ml) and 98 g of 2-ethyl-3,7-dimethyl-6-(4-(trifluoromethoxy)phenoxy)quinolin-4(1H)-one were charged into a glass flask equipped with a stirring device, a thermometer, a reflux condenser, and a calcium chloride tube and having a volume of 2000 ml under a nitrogen atmosphere, and the mixture was cooled to 15° C. 55% sodium hydride (18.2 g) was added thereto, and the mixture was stirred at 15 to 20° C. for one hr. Methyl chloroformate (32.1 g) was added dropwise, 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 a 10-L plastic container, and the mixture was stirred at room temperature for 2 hr. The precipitated solid was collected by a suction filter and was washed with n-hexane and water. The solid was dried in vacuo to give 2-ethyl-3,7-dimethyl-6-(4-(trifluoromethoxy)phenoxy)quinolin-4-yl methyl carbonate (103.3 g, yield 91.4%).

Workup

  1. customequipped with a stirring device
  2. waitto proceed at room temperature for one hr
  3. stirringthe mixture was stirred at room temperature for 2 hr
  4. customThe precipitated solid was collected by a suction
  5. filtrationfilter
  6. washwas washed with n-hexane and water
  7. customThe solid was dried in vacuo

Sources & evidence

ORD record
ord-c93b792a0d774eb6869aba272a789b5a
Source dataset
uspto-grants-2015_09
Patent number
US09126934B2

Reaction notes

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