1,2-Cyclohexanedione → HCID 67377466、化合物

HRID 877475ノート

反応式

HRID 877475 の反応式
Cl.[Cl:2][C:3]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:4]=1[NH:10]N.[CH2:12]1[CH2:19][C:17](=O)[C:15](=[O:16])[CH2:14][CH2:13]1>CO.CC(O)=O.Cl>[Cl:2][C:3]1[CH:8]=[C:7]([F:9])[CH:6]=[C:5]2[C:4]=1[NH:10][C:14]1[C:15](=[O:16])[CH2:17][CH2:19][CH2:12][C:13]2=1

参加物

6

反応物 2

HCID 130061,2-CyclohexanedioneHCID 247210492-Chloro-4-fluorophenylhydrazine hydrochloride

生成物 1

HCID 67377466HCID 67377466、化合物収率 56.1%

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 313Hydrochloric Acid溶媒HCID 887Methanol溶媒

反応条件

温度
60 °C

実験手順

To 2-chloro-4-fluoro phenyl hydrazine hydrochloride (0.3 g, 1.5 mmol) in MeOH (2.5 mL), a solution of 1,2-cyclohexadione (0.17 g, 1.5 mmol) in AcOH (2.5 mL) and conc. HCl (1 mL) were added. The resulting mixture was stirred at 60° C. for 12 h, then cooled to room temperature and MeOH was removed in vacuo. Water (25 mL) was added and the reaction mixture was basified with NaHCO3 (pH 8). The crude residue was extracted with EtOAc (2×30 mL). The combined organic extracts were washed with water (50 mL), dried over Na2SO4 and concentrated in vacuo to give the crude material which was purified by silica gel chromatography [EtOAc-hexane (1:19) as eluant] to afford the title compound (0.2 g, 55%). 1H NMR (200 MHz, CDCl3, δ in ppm) 8.84 (bs, 1H), 7.26-7.17 (m, 2H), 2.99-2.93 (t, J=6.0 Hz, 2H), 2.70-2.64 (q, J=7.4, 5.8 Hz, 2H), 2.34-2.21 (m, 2H).

後処理

  1. temperaturecooled to room temperature
  2. customMeOH was removed in vacuo
  3. additionWater (25 mL) was added
  4. extractionThe crude residue was extracted with EtOAc (2×30 mL)
  5. washThe combined organic extracts were washed with water (50 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customto give the crude material which
  9. customwas purified by silica gel chromatography [EtOAc-hexane (1:19) as eluant]

出典と根拠

ORDレコード
ord-726e0f9208c94921abcd92a94f5bffc7
出典データセット
uspto-grants-2015_03
特許番号
US08987319B2

反応ノート

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