Methyl chloroformate → Flometoquin

HRID 2273843Notes

Reaction equation

HRID 2273843 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

Dimethyl acetamide (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 to a glass vessel equipped with a stirring device, a thermometer, and a reflux condenser and having a volume of 1000 ml 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 vessel, and the mixture was stirred at room temperature for 2 hr. The precipitated solid was collected by a suction filter and was washed with water. The solid was dried in vacuo to give 2-ethyl-3,7-dimethyl-6-(4-(trifluoromethoxy)phenoxy)quinolin-4-yl methyl carbonate (149.5 g, yield 98.8%).

Workup

  1. customequipped with a stirring device
  2. customcontained in a 5-L plastic vessel
  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 water
  7. customThe solid was dried in vacuo

Sources & evidence

ORD record
ord-e28d0b1369ee4e0d9055efaeb6837d94
Source dataset
uspto-grants-2015_09
Patent number
US09126934B2

Reaction notes

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