Hydrochloric Acid → 2-Ethoxyethyl 2-methyl-4-(3-nitrophenyl)-5-ethoxycarbonyl-6-hydroxymethyl-1,4-dihydropyridine-3-carboxylate

HRID 1759083노트

반응식

HRID 1759083 반응식
[CH3:1][C:2]1[NH:3][C:4]([CH:30]=[O:31])=[C:5]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:6]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-:24])=[O:23])[CH:17]=2)[C:7]=1[C:8]([O:10][CH2:11][CH2:12][O:13][CH2:14][CH3:15])=[O:9].[BH4-].[Na+].Cl>C(O)C>[CH3:1][C:2]1[NH:3][C:4]([CH2:30][OH:31])=[C:5]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:6]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-:24])=[O:23])[CH:17]=2)[C:7]=1[C:8]([O:10][CH2:11][CH2:12][O:13][CH2:14][CH3:15])=[O:9]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 133883552-Ethoxyethyl 2-methyl-4-(3-nitrophenyl)-5-ethoxycarbonyl-6-formyl-1,4-dihydropyridine-3-carboxylate

생성물 1

HCID 130921522-Ethoxyethyl 2-methyl-4-(3-nitrophenyl)-5-ethoxycarbonyl-6-hydroxymethyl-1,4-dihydropyridine-3-carboxylate수율 79.3%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a suspension of 2-ethoxyethyl 2-methyl-4-(3-nitrophenyl)-5-ethoxycarbonyl-6-formyl-1,4-dihydropyridine-3-carboxylate (1.13 g) in ethanol (15 ml) was added sodium borohydride (80 mg) with stirring under ice-cooling, and this mixture was further stirred for an hour at the same temperature. The reaction mixture was adjusted with dilute hydrochloric acid to pH 6 under ice-cooling and then the solvent was distilled off. To the residue was added water and the aqueous mixture was extracted with diethyl ether. The extract was washed with water and dried over magnesium sulfate. Removal of the solvent gave an oil, which was crystallized by treating with n-hexane. These were recrystallized from a mixture of diethyl ether and n-hexane to give pure crystals (900 mg) of 2-ethoxyethyl 2-methyl-4-(3-nitrophenyl)-5-ethoxycarbonyl-6-hydroxymethyl-1,4-dihydropyridine-3-carboxylate, m.p. 99° to 100° C.

후처리

  1. temperaturecooling
  2. stirringthis mixture was further stirred for an hour at the same temperature
  3. temperaturecooling
  4. distillationthe solvent was distilled off
  5. additionTo the residue was added water
  6. extractionthe aqueous mixture was extracted with diethyl ether
  7. washThe extract was washed with water
  8. dry with materialdried over magnesium sulfate
  9. customRemoval of the solvent
  10. customgave an oil, which
  11. customwas crystallized
  12. additionby treating with n-hexane
  13. customThese were recrystallized from a mixture of diethyl ether and n-hexane

출처 및 근거

ORD 기록
ord-283220f77c3f4158969ac380d6bda1fe
출처 데이터셋
uspto-grants-1982_07
특허 번호
US04338322

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