Sodium Hydroxide → 2,6-Dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid monomethyl ester

HRID 622174

반응식

HRID 622174 반응식
[CH3:1][C:2]1[NH:3][C:4]([CH3:25])=[C:5]([C:21]([O:23][CH3:24])=[O:22])[CH:6]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=2)[C:7]=1[C:8]([O:10]C)=[O:9].[OH-].[Na+]>CO.O>[CH3:24][O:23][C:21]([C:5]1[CH:6]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=2)[C:7]([C:8]([OH:10])=[O:9])=[C:2]([CH3:1])[NH:3][C:4]=1[CH3:25])=[O:22]

참가 물질

5

반응물 2

HCID 14798Sodium HydroxideHCID 89082m-Nifedipine

생성물 1

HCID 1733222,6-Dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid monomethyl ester수율 66.2%

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매2회

실험 절차

Dimethyl 2,6-dimethyl-4-(m-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate (17.3 g, 0.05 mole) is suspended in methanol (280 ml) and thereto a solution of NaOH (15.9 g, 0.4 mole) in water (52 ml) is added at room temperature under stirring. The reaction mixture is stirred at reflux temperature for 5 hours, cooled, water (1050 ml) is added under stirring and the resulting mixture is filtered. The precipitate is the unreacted starting compound, i.e. dimethyl 2,6-dimethyl-4-(m-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate. To the clear filtrate activated carbon (1 g) is added and the mixture is stirred at 50°-60° C. for 30 minutes. After cooling the activated carbon is filtered off, the filtrate is acidified with 1 n HCl to pH 2.5 and the precipitate is filtered and washed with water (2×15 ml). Thus, there is obtained the pure title compound (11 g, 66%), m.p. 202°-206° C.

후처리

  1. stirringThe reaction mixture is stirred
  2. temperatureat reflux temperature for 5 hours
  3. temperaturecooled
  4. stirringunder stirring
  5. filtrationthe resulting mixture is filtered
  6. additionTo the clear filtrate activated carbon (1 g) is added
  7. stirringthe mixture is stirred at 50°-60° C. for 30 minutes
  8. temperatureAfter cooling the activated carbon
  9. filtrationis filtered off
  10. filtrationthe precipitate is filtered
  11. washwashed with water (2×15 ml)

출처 및 근거

ORD 기록
ord-d443c5afe32943b2b54ecbf8842c0b7c
출처 데이터셋
uspto-grants-1988_09
특허 번호
US04769465

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