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

HRID 561146ノート

反応式

HRID 561146 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 178418332HCID 178418332、化合物溶媒

反応条件

温度
-78 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-94f0ffc81e3045b58b6fbfa2d8edb824
出典データセット
uspto-grants-2011_11
特許番号
US08063221B2

反応ノート

読み込み中…