Hydrochloric Acid → FR 7534

HRID 1759077ノート

反応式

HRID 1759077 の反応式
[CH3:1][C:2]1[NH:3][C:4]([CH:27]=[O:28])=[C:5]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:6]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=2)[C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9].[BH4-].[Na+].Cl>C(O)C>[CH3:1][C:2]1[NH:3][C:4]([CH2:27][OH:28])=[C:5]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:6]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=2)[C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 13388353HCID 13388353、化合物

生成物 1

HCID 173874FR 7534収率 64.9%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a suspended solution of diethyl 2-methyl-4-(3-nitrophenyl)-6-formyl-1,4-dihydropyridine-3,5-dicarboxylate (233 mg) in ethanol (10 ml) was added sodium borohydride (22.7 mg) at 0° to 5° C. under stirring and this mixture was further stirred at about 5° C. for an hour and 10 minutes. After the reaction, the mixture was adjusted to pH 4 to 5 with 0.1 N-hydrochloric acid, and then the solvent was removed under reduced pressure. The residue was extracted with ethyl acetate and the extract was washed with water and dried over magnesium sulfate. The extract was concentrated under reduced pressure and the residue was crystallized by treating with a mixture of diethyl ether and n-hexane. The precipitated crystals were collected by filtration, dried and recrystallized from a mixture of diethyl ether and n-hexane to give crystals of diethyl 2-methyl-4-(3-nitrophenyl)-6-hydroxymethyl-1,4-dihydropyridine-3,5-dicarboxylate (152 mg), m.p. 141° to 142.5° C.

後処理

  1. stirringthis mixture was further stirred at about 5° C. for an hour and 10 minutes
  2. customAfter the reaction
  3. customthe solvent was removed under reduced pressure
  4. extractionThe residue was extracted with ethyl acetate
  5. washthe extract was washed with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationThe extract was concentrated under reduced pressure
  8. customthe residue was crystallized
  9. additionby treating with a mixture of diethyl ether and n-hexane
  10. filtrationThe precipitated crystals were collected by filtration
  11. customdried
  12. customrecrystallized from a mixture of diethyl ether and n-hexane

出典と根拠

ORDレコード
ord-68a24daa5b3540fa93f563d7faad4abf
出典データセット
uspto-grants-1982_07
特許番号
US04338322

反応ノート

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