Diisopropyl Ether → Ethyl 1-(chloromethyl)methylamino-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate

HRID 1708548Notes

Reaction equation

HRID 1708548 reaction equation
C(O[CH2:4][CH2:5][NH:6][N:7]1[C:16]2[C:11](=[CH:12][C:13]([F:19])=[C:14]([F:18])[C:15]=2[F:17])[C:10](=[O:20])[C:9]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:8]1)C.[Cl:26]C([SiH3])(Cl)Cl.C(OC(C)C)(C)C>C(#N)C>[Cl:26][CH2:4][CH2:5][NH:6][N:7]1[C:16]2[C:11](=[CH:12][C:13]([F:19])=[C:14]([F:18])[C:15]=2[F:17])[C:10](=[O:20])[C:9]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:8]1

Participants

5

Reactant 3

HCID 7914Diisopropyl EtherHCID 18959438Ethyl 1-(ethoxymethyl)methylamino-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylateHCID 71317501CID 71317501

Product 1

HCID 67849549Ethyl 1-(chloromethyl)methylamino-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of ethyl 1-(ethoxymethyl)methylamino-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate (200 mg) in dry acetonitrile (2.0 ml) was added trichloromethylsilane (65.8 μl) under ice -cooling and the mixture was stirred for 30 minutes, and then for 10 minutes at room temperature. To the reaction mixture was added diisopropyl ether (10 ml), which was then stirred for 15 minutes at ambient temperature. The precipitate was collected by filtration and washed with diisopropyl ether and dried in vacuo over phosphorus pentaoxide to give ethyl 1-(chloromethyl)methylamino-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate (145 mg).

Workup

  1. waitfor 10 minutes at room temperature
  2. stirringwas then stirred for 15 minutes at ambient temperature
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with diisopropyl ether
  5. dry with materialdried in vacuo over phosphorus pentaoxide

Sources & evidence

ORD record
ord-5ba40038d209486dbbe43c1f61145e26
Source dataset
uspto-grants-1994_10
Patent number
US05359066

Reaction notes

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