Sodium Bicarbonate → Ethyl 6,7,8-trifluoro-1-(methylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 1708541Notes

Reaction equation

HRID 1708541 reaction equation
Cl.[F:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([F:14])[C:12]=1[F:13])[N:9]([NH:15][CH3:16])[CH:8]=[C:7]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:6]2=[O:22].C(=O)([O-])O.[Na+]>ClCCl>[F:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([F:14])[C:12]=1[F:13])[N:9]([NH:15][CH3:16])[CH:8]=[C:7]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:6]2=[O:22]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 67849559HCID 67849559, compound

Product 1

HCID 11098599Ethyl 6,7,8-trifluoro-1-(methylamino)-4-oxo-1,4-dihydroquinoline-3-carboxylateYield 97.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 6,7,8-trifluoro-1-methylamino-1,4-dihydro -4-oxoquinoline-3-carboxylate hydrochloride(5.91 g)in dichloromethane (100 ml) was added a saturated aqueous sodium hydrogencarbonate solution (50 ml) and the mixture was stirred at ambient temperature for 30 minutes. The organic layer was washed with brine (50 ml), dried over magnesium sulfate, and concentrated under reduced pressure to give a solid. The solid was recrystallized from dichloromethane-n-hexane to give ethyl 6,7,8-trifluoro-1-methylamino-1,4-dihydro-4-oxoquinoline-3-carboxylate (5.14 g).

Workup

  1. washThe organic layer was washed with brine (50 ml)
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customto give a solid
  5. customThe solid was recrystallized from dichloromethane-n-hexane

Sources & evidence

ORD record
ord-5a48949633a54f27a9bea7505c9f760d
Source dataset
uspto-grants-1994_10
Patent number
US05359066

Reaction notes

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