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

HRID 561146노트

반응식

HRID 561146 반응식
[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

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 8028Tetrahydrofuran2회HCID 10666701Ethyl 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-5-nitro-4-oxoquinoline-3-carboxylate

생성물 1

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

시약·촉매·용매 1

HCID 178418332HCID 178418332, 화합물용매

반응 조건

온도
-78 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-94f0ffc81e3045b58b6fbfa2d8edb824
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063221B2

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