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

HRID 561151ノート

反応式

HRID 561151 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>C1COCC1.C1([Mg]Br)C=CC=CC=1>[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[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:2][CH2:3]1

参加物

5

反応物 2

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

生成物 1

HCID 66999747Ethyl 1-cyclopropyl-6,7-difluoro-1,2,3,4-tetrahydro-8-methoxy-5-nitro-4-oxo-2-phenylquinoline-3-carboxylate収率 169.9%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 178418255HCID 178418255、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 (3.00 g, 8.15 mmol) and cuprous iodide (467 mg, 2.45 mmol) in THF (80 mL), 2 M phenylmagnesium bromide in THF (6.10 mL, 12.2 mmol) was added under argon atmosphere at −78° C. After stirred at −78° C. for 1 h and at room temperature for 2 h, the reaction mixture was poured into ice-water (400 mL) and concentrated HCl (40 mL) was added to stirred for 30 min. The crude product was extracted with EtOAc, washed with saturated aq. NaHCO3 and brine, dried over MgSO4 and the solvent was removed in vacuo. The crude product was purified by column chromatography (Hexane:EtOAc 40:1→10:1) to yield ethyl 1-cyclopropyl-6,7-difluoro-1,2,3,4-tetrahydro-8-methoxy-5-nitro-4-oxo-2-phenylquinoline-3-carboxylate (3.09 g, 85%) 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 saturated aq. NaHCO3 and 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 40:1→10:1)

出典と根拠

ORDレコード
ord-88fb22268caa4d77868ca17d54f49a73
出典データセット
uspto-grants-2011_11
特許番号
US08063221B2

反応ノート

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