Hydrochloric Acid → 2,6-Dimethyl-3,5-dicarboxy-4-(2-nitrophenyl)-1,4-dihydropyridine

HRID 2418258노트

반응식

HRID 2418258 반응식
[C:1]([O-:7])(=[O:6])[CH2:2][C:3]([CH3:5])=O.[N+:8]([C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1[CH:13]=O)([O-:10])=[O:9].N1CCCCC1.Cl.[NH2:26]/[C:27](/[CH3:32])=[CH:28]\[C:29]([O-:31])=[O:30]>C1C=CC=CC=1>[CH3:5][C:3]1[NH:26][C:27]([CH3:32])=[C:28]([C:29]([OH:31])=[O:30])[CH:13]([C:12]2[CH:15]=[CH:16][CH:17]=[CH:18][C:11]=2[N+:8]([O-:10])=[O:9])[C:2]=1[C:1]([OH:7])=[O:6]

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 8082PiperidineHCID 111012-NitrobenzaldehydeHCID 6971017AcetoacetateHCID 222503863-Aminocrotonate

생성물 1

HCID 120733112,6-Dimethyl-3,5-dicarboxy-4-(2-nitrophenyl)-1,4-dihydropyridine수율 72.6%

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

In 100 ml of benzene were dissolved 10 g of 2-nitratoethy acetoacetate, 7.91 g of 2-nitrobenzaldehyde and 0.7 ml of piperidine. The solution was reacted under azeotropic dehydration for 1.5 hours, and poured into ice water. Dilute hydrochloric acid was added, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed, in turn, with 15% aqueous sodium hydrogen sulfite solution, 15% aqueous sodium carbonate solution and saturated aqueous sodium chloride solution, and then dried over anhydrous sodium sulfate. Evaporation of the solvent gave a residue, to which 10.68 g of 3-nitratopropyl 3-aminocrotonate was then added. The mixture was heated at 75°-85° C. for 4 hours with stirring, and ice water was poured into this mixture. The mixture was extracted with dichloromethane, and the dichloromethane layer was washed with water and dried over anhydrous sodium sulfate. Evaporation of the solvent gave a residue which was then subjected to column chromatography on silica gel (eluted with dichloromethane) and recrystallized from ether to obtain 12.1 g of 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-(2-nitratoethyl) ester-5-(3-nitratopropyl) ester.

후처리

  1. customThe solution was reacted under azeotropic dehydration for 1.5 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed, in turn, with 15% aqueous sodium hydrogen sulfite solution, 15% aqueous sodium carbonate solution and saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. customEvaporation of the solvent
  6. customgave a residue
  7. temperatureThe mixture was heated at 75°-85° C. for 4 hours
  8. extractionThe mixture was extracted with dichloromethane
  9. washthe dichloromethane layer was washed with water
  10. dry with materialdried over anhydrous sodium sulfate
  11. customEvaporation of the solvent
  12. customgave a residue which
  13. customrecrystallized from ether

출처 및 근거

ORD 기록
ord-bede06cd18754317a9b52fe3e08b36df
출처 데이터셋
uspto-grants-1984_09
특허 번호
US04472411

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