2-Chloro-1-pyrroline → 2-[(2-Methyl-4-(N-methylacetamido)phenyl)amino]-1-pyrroline, hydrochloride

HRID 484806

반응식

HRID 484806 반응식
[Cl:1][C:2]1[CH2:6][CH2:5][CH2:4][N:3]=1.[CH3:7][C:8]1[CH:14]=[C:13]([N:15]([CH3:19])[C:16](=[O:18])[CH3:17])[CH:12]=[CH:11][C:9]=1[NH2:10]>C1(C)C=CC=CC=1>[ClH:1].[CH3:7][C:8]1[CH:14]=[C:13]([N:15]([CH3:19])[C:16](=[O:18])[CH3:17])[CH:12]=[CH:11][C:9]=1[NH:10][C:2]1[CH2:6][CH2:5][CH2:4][N:3]=1

참가 물질

4

반응물 2

HCID 135201412-Chloro-1-pyrrolineHCID 202723852-Methyl-4-(N-methylacetamido)aniline

생성물 1

HCID 704655352-[(2-Methyl-4-(N-methylacetamido)phenyl)amino]-1-pyrroline, hydrochloride

시약·촉매·용매 1

HCID 1140Toluene용매3회

실험 절차

A mixture of 2-chloro-1-pyrroline, prepared as in Example 1 using toluene instead of acetonitrile, and 0.8 g of the product aniline of Example 38 in anhydrous toluene was heated at reflux for five hours. Upon cooling the toluene was removed by decanting and the residue was partitioned between water and dichloromethane. The aqueous layer was made alkaline with 50% sodium hydroxide and extracted with dichloromethane. The organic phase was dried over potassium carbonate, filtered, concentrated to an oil. The crude product was purified by low-pressure chromatography on silica gel, using as eluent 74:25:1 dichloromethane/ethanol/concentrated aqueous ammonia. The oily product was dissolved in ethanol and acidified with HCl in isopropyl alcohol. Addition of diethyl ether produced the title compound as the hydrochloride salt, m.p. 367°-370°. Structure assignment was supported by the nmr spectrum and by elemental analysis.

후처리

  1. temperaturewas heated
  2. temperatureat reflux for five hours
  3. customwas removed
  4. customby decanting
  5. customthe residue was partitioned between water and dichloromethane
  6. extractionextracted with dichloromethane
  7. dry with materialThe organic phase was dried over potassium carbonate
  8. filtrationfiltered
  9. concentrationconcentrated to an oil
  10. customThe crude product was purified by low-pressure chromatography on silica gel
  11. dissolutionThe oily product was dissolved in ethanol
  12. additionAddition of diethyl ether

출처 및 근거

ORD 기록
ord-3e3dbc1a8e294880ae5cdf5d78117a7d
출처 데이터셋
uspto-grants-1985_08
특허 번호
US04533739

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