Methyl chloroformate → Flometoquin

HRID 384835Notes

Reaction equation

HRID 384835 reaction equation
CC(N(C)C)=O.CC(C)([O-])C.[Na+].[CH2:13]([C:15]1[NH:16][C:17]2[C:22]([C:23](=[O:26])[C:24]=1[CH3:25])=[CH:21][C:20]([O:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][C:35]([F:38])([F:37])[F:36])=[CH:30][CH:29]=1)=[C:19]([CH3:39])[CH:18]=2)[CH3:14].Cl[C:41]([O:43][CH3:44])=[O:42]>O>[C:41](=[O:42])([O:43][CH3:44])[O:26][C:23]1[C:22]2[C:17](=[CH:18][C:19]([CH3:39])=[C:20]([O:27][C:28]3[CH:33]=[CH:32][C:31]([O:34][C:35]([F:36])([F:37])[F:38])=[CH:30][CH:29]=3)[CH:21]=2)[N:16]=[C:15]([CH2:13][CH3:14])[C:24]=1[CH3:25]

Participants

6

Reactant 4

HCID 6586Methyl chloroformateHCID 31374DimethylacetamideHCID 23676156Sodium t-butoxideHCID 67119408HCID 67119408, compound

Product 1

HCID 67119441FlometoquinYield 98.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Dimethylacetamide (694 ml), 35.2 g of sodium t-butoxide, and 131 g of 2-ethyl-3,7-dimethyl-6-(4-(trifluoromethoxy)phenoxy)quinolin-4(1H)-one were added into a 1000-ml glass flask equipped with a stirring device, a thermometer, and a reflux condenser under a nitrogen atmosphere, and the mixture was stirred at room temperature. Methyl chloroformate (34.4 g) was added dropwise thereto, and a reaction was allowed to proceed at room temperature for one hr. The reaction mixture was poured into 1735 ml of water contained in a 5-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. The solid was dried under the reduced pressure to give 2-ethyl-3,7-dimethyl-6-(4-(trifluoromethoxy)phenoxy)quinolin-4-yl methyl carbonate (149.5 g, yield: 98.8%). 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. stirringthe mixture was stirred at room temperature for two hr
  3. filtrationThe precipitated solid was collected by filtration through a suction
  4. filtrationfilter
  5. washwas washed with water
  6. customThe solid was dried under the reduced pressure

Sources & evidence

ORD record
ord-f77aaaf2747c4ce89b768e9f1754091d
Source dataset
uspto-grants-2013_02
Patent number
US08367833B2

Reaction notes

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