1,2-Cyclohexanedione → HCID 67377466, 화합물

HRID 877475노트

반응식

HRID 877475 반응식
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

참가 물질

6

반응물 2

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

생성물 1

HCID 67377466HCID 67377466, 화합물수율 56.1%

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 313Hydrochloric Acid용매HCID 887Methanol용매

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온도
60 °C

실험 절차

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).

후처리

  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]

출처 및 근거

ORD 기록
ord-726e0f9208c94921abcd92a94f5bffc7
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08987319B2

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