Acetone → 7-isopropyl-2-methyl-1H-indole

HRID 226087

반응식

HRID 226087 반응식
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10]N)([CH3:3])[CH3:2].Cl.[CH3:13][C:14]([CH3:16])=O>CCO>[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:5]=1[NH:10][C:14]([CH3:16])=[CH:13]2)([CH3:3])[CH3:2]

참가 물질

5

반응물 3

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 7045932-Isopropylphenylhydrazine

생성물 1

HCID 222505907-isopropyl-2-methyl-1H-indole수율 20%

시약·촉매·용매 1

HCID 702Ethanol촉매

반응 조건

온도
140 °C

실험 절차

To a solution of (2-isopropyl-phenyl)-hydrazine 7.60 g, 0.0506 mol) (Asselin et al., J. Med. Chem. 1976, 19, 787-792) and acetone (100 mL) is added 1M HCl in EtOH (2 drops). The solution is heated at a reflux overnight. The solution is concentrated, dissolved in toluene (100 mL) and concentrated. The residue is dissolved in o-xylene (100 mL) and ZnCl2 (8.3 g) is added. The solution is heated at 140° C. for 2 hours, cooled to ambient temperature, diluted with EtOAc (200 mL), washed with sat. NH4Cl, dried over Na2SO4, filtered and concentrated. The residue is purified by ISCO (5%-15% EtOAc gradient to furnish the title compound (1.76 g, 10.16 mmol, 20%). 1H NMR (CDCl3), δ 1.43 (d, J=7.0 Hz, 6H), 2.50 (s, 3H), 3.17-3.29 (m, 1H), 6.24-6.27 (m, 1H), 7.02 (d, J=7.1 Hz, 1H), 7.07 (dd, J=7.5, 7.1 Hz, 1H), 7.39 (d, J=7.5 Hz, 1H), 7.85 (bs, 1H) ppm. LC/MS (m/z): calcd. for C12H15N (M+H)+: 174.1. found: 174.1.

후처리

  1. temperatureThe solution is heated at a reflux overnight
  2. concentrationThe solution is concentrated
  3. dissolutiondissolved in toluene (100 mL)
  4. concentrationconcentrated
  5. dissolutionThe residue is dissolved in o-xylene (100 mL)
  6. additionZnCl2 (8.3 g) is added
  7. temperaturecooled to ambient temperature
  8. additiondiluted with EtOAc (200 mL)
  9. washwashed with sat. NH4Cl
  10. dry with materialdried over Na2SO4
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customThe residue is purified by ISCO (5%-15% EtOAc gradient

출처 및 근거

ORD 기록
ord-45dcee8e0f6f4d19ac5a7bcf9727f8c0
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07557103B2

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