Hydrochloric Acid → Ethyl 1-cyclopropyl-6,7-difluoro-1,2,3,4-tetrahydro-8-methoxy-2-methyl-5-nitro-4-oxoquinoline-3-carboxylate

HRID 561146Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 561146
[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([N+:18]([O-:20])=[O:19])[C:10]([F:17])=[C:11]([F:16])[C:12]=3[O:14][CH3:15])[C:7](=[O:21])[C:6]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:5]2)[CH2:3][CH2:2]1.Cl.[CH2:28]1COCC1>C[Mg]Cl>[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([N+:18]([O-:20])=[O:19])[C:10]([F:17])=[C:11]([F:16])[C:12]=3[O:14][CH3:15])[C:7](=[O:21])[CH:6]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:5]2[CH3:28])[CH2:2][CH2:3]1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 8028Tetrahydrofuran2×HCID 10666701Ethyl 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-5-nitro-4-oxoquinoline-3-carboxylate

Produkt 1

HCID 66999917Ethyl 1-cyclopropyl-6,7-difluoro-1,2,3,4-tetrahydro-8-methoxy-2-methyl-5-nitro-4-oxoquinoline-3-carboxylateAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 178418332HCID 178418332, VerbindungLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a stirred solution of ethyl 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-5-nitro-4-oxoquinoline-3-carboxylate (2.50 g, 6.79 mmol) and cuprous iodide (389 mg, 2.04 mmol) in THF (70 mL), 3 M methylmagnesium chloride in THF (3.40 mL, 10.2 mmol) was added under argon atmosphere at −78° C. After stirred at −78° C. for 1 h and at room temperature for 1 h, the reaction mixture was poured into ice-water (300 mL) and concentrated HCl (30 mL) was added to stirred for 30 min. The crude product was extracted with EtOAc, washed with brine, dried over MgSO4 and the solvent was removed in vacuo. The crude product was purified by column chromatography (Hexane:EtOAc 20:1→5:1) to yield ethyl 1-cyclopropyl-6,7-difluoro-1,2,3,4-tetrahydro-8-methoxy-2-methyl-5-nitro-4-oxoquinoline-3-carboxylate (1.44 g, 55%) as a yellow solid.

Aufarbeitung

  1. additionwas added
  2. stirringto stirred for 30 min
  3. extractionThe crude product was extracted with EtOAc
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. customthe solvent was removed in vacuo
  7. customThe crude product was purified by column chromatography (Hexane:EtOAc 20:1→5:1)

Quellen und Nachweise

ORD-Eintrag
ord-94f0ffc81e3045b58b6fbfa2d8edb824
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063221B2

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