Hydrochloric Acid → Methyl 6,7,8-trifluoro-1-methylamino-1,4-dihydro-4-oxoquinoline-3-carboxylate

HRID 1708545Notes

Reaction equation

HRID 1708545 reaction equation
C(OCC)(=O)C.Cl.C(O[C:13]([N:15]([N:17]1[C:26]2[C:21](=[CH:22][C:23]([F:29])=[C:24]([F:28])[C:25]=2[F:27])[C:20](=[O:30])[C:19]([C:31]([O:33][CH3:34])=[O:32])=[CH:18]1)C)=O)(C)(C)C.C(=O)([O-])O.[Na+]>O.C(Cl)Cl>[F:29][C:23]1[CH:22]=[C:21]2[C:26](=[C:25]([F:27])[C:24]=1[F:28])[N:17]([NH:15][CH3:13])[CH:18]=[C:19]([C:31]([O:33][CH3:34])=[O:32])[C:20]2=[O:30]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 18959448methyl 1-(N-tert-butoxycarbonyl-N-methylamino)-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate

Product 1

HCID 15247753Methyl 6,7,8-trifluoro-1-methylamino-1,4-dihydro-4-oxoquinoline-3-carboxylateYield 50.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To ethyl acetate solution (55 ml) of 4N hydrochloric acid, was added methyl 1-(N-tert-butoxycarbonyl-N-methylamino)-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate (10.85 g) with ice-cooling, and the mixture was stirred for one hour at the same temperature and then for 14 hours at room temperature. The mixture was concentrated under reduced pressure to obtain a solid. The solid was poured into a mixture comprising methylene chloride (150 ml) and water (150 ml). The suspension was neutralized with sodium hydrogencarbonate. The precipitates were taken out by filtration, washed with water and dried with phosphorus pentaoxide to obtain a solid. The solid was recrystallized from a liquid mixture of methylene chloride and diisopropyl ether to obtain methyl 6,7,8-trifluoro-1-methylamino-1,4-dihydro-4-oxoquinoline-3-carboxylate (4.05 g).

Workup

  1. temperaturecooling
  2. waitfor 14 hours at room temperature
  3. concentrationThe mixture was concentrated under reduced pressure
  4. customto obtain a solid
  5. filtrationThe precipitates were taken out by filtration
  6. washwashed with water
  7. dry with materialdried with phosphorus pentaoxide
  8. customto obtain a solid
  9. customThe solid was recrystallized from a liquid mixture of methylene chloride and diisopropyl ether

Sources & evidence

ORD record
ord-5824633f071a4d83a2824d5e4ffc7c25
Source dataset
uspto-grants-1994_10
Patent number
US05359066

Reaction notes

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