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Benzene → Diethyl 2-methyl-4-(2-nitrophenyl)-6-acetoxymethyl-1,4-dihydropyridine-3,5-dicarboxylate

HRID 614618
ノート
印刷プレビュー

反応式

HRID 614618 の反応式
C1C=CC=CC=1.[CH3:7][C:8]1[NH:9][C:10]([CH2:33][OH:34])=[C:11]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[N+:25]([O-:27])=[O:26])[C:13]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15].[C:35](Cl)(=[O:37])[CH3:36]>N1C=CC=CC=1.C(Cl)Cl>[CH3:7][C:8]1[NH:9][C:10]([CH2:33][O:34][C:35](=[O:37])[CH3:36])=[C:11]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[N+:25]([O-:27])=[O:26])[C:13]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 241BenzeneHCID 6367Acetyl chlorideHCID 133883402-Hydroxymethyl-6-methyl-4-(nitrophenyl)-3,5-diethoxycarbonyl-1,4-dihydropyridine

生成物 1

HCID 13388345Diethyl 2-methyl-4-(2-nitrophenyl)-6-acetoxymethyl-1,4-dihydropyridine-3,5-dicarboxylate収率 68.4%

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒
HCID 6344
Dichloromethane
溶媒

実験手順

((5) To a mixture of diethyl 2-methyl-4-(2-nitrophenyl)-6-hydroxymethyl-1,4-dihydropyridine-3,5-dicarboxylate (2.35 g) in pyridine (30 ml), was dropwise added a solution of acetyl chloride (942 mg) in methylene chloride (5 ml) under stirring and ice-cooling over the period of 7 minutes. The mixture was further stirred for 70 minutes at room temperature. The pyridine was distilled off under reduced pressure and ethyl acetate was added to the residue. The resultant mixture was washed twice with water adjusted to pH 4 with hydrochloric acid and then an aqueous solution of sodium chloride, dried and concentrated under reduced pressure to give an oily substance. This oily substance was crystallized by treating with a mixture of diethyl ether and a small amaunt of n-hexane, and collected crude crystals (2.5 g) were washed with n-hexane and thus obtained crystals were recrystallized from diethyl ether to give pure crystals (1.78 g) of diethyl 2-methyl-4-(2-nitrophenyl)-6-acetoxymethyl-1,4-dihydropyridine-3,5-dicarboxylate, m.p. 89° to 90° C.

後処理

  1. temperatureice-cooling over the period of 7 minutes
  2. stirringThe mixture was further stirred for 70 minutes at room temperature
  3. distillationThe pyridine was distilled off under reduced pressure and ethyl acetate
  4. additionwas added to the residue
  5. washThe resultant mixture was washed twice with water
  6. dry with materialan aqueous solution of sodium chloride, dried
  7. concentrationconcentrated under reduced pressure
  8. customto give an oily substance
  9. customThis oily substance was crystallized
  10. additionby treating with a mixture of diethyl ether
  11. customa small amaunt of n-hexane, and collected crude crystals (2.5 g)
  12. washwere washed with n-hexane and thus obtained crystals
  13. customwere recrystallized from diethyl ether

出典と根拠

ORDレコード
ord-23e09eb7a49a4c058e4dfb4d6121dd9b
出典データセット
uspto-grants-1979_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04145432

反応ノート

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