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Hydrazine → 2-Aminoethyl methyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate

HRID 256722
ノート
印刷プレビュー

反応式

HRID 256722 の反応式
[CH3:1][C:2]1[NH:3][C:4]([CH3:37])=[C:5]([C:21]([O:23][CH2:24][CH2:25][N:26]2C(=O)C3=CC=CC=C3C2=O)=[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][CH3:11])=[O:9].O.NN.NN>C(O)C.C(Cl)Cl>[CH3:1][C:2]1[NH:3][C:4]([CH3:37])=[C:5]([C:21]([O:23][CH2:24][CH2:25][NH2:26])=[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][CH3:11])=[O:9]
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 9321HydrazineHCID 24654Hydrazine hydrate (1:1)HCID 137998311,4-Dihydro-2,6-dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-5-(2-phthalimidoethoxy)carbonyl-pyridine

生成物 1

HCID 135634192-Aminoethyl methyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate収率 98.7%

試薬・触媒・溶媒 2

HCID 702Ethanol
溶媒
HCID 6344Dichloromethane溶媒

実験手順

A solution of 2.32 g (4.59 mmol) of (±)-2,6-dimethyl-3-carbomethoxy-4-(3-nitrophenyl)-5-(2-phthalimidoethyloxycarbonyl)-1,4-dihydropyridine and 344 mg of hydrazine monohydrate in 100 ml of ethanol is heated at reflux for 2 hr. TLC indicates the reaction is incomplete so another 1.5 equivalents of hydrazine monhydrate is added and the mixture refluxed for an additional hr. After cooling, the precipitate is collected by filtration, washed with ethanol, and the filtrate evaporated under vacuum to leave a yellow solid. This solid is taken up in 125 ml of CH2Cl2, washed twice with 0.5N KOH, once with water, dried (MgSO4), filtered, and the solvent removed under vacuum to give 1.70 g of (±)-2,6-dimethyl-3-carbomethoxy-4-(3-nitrophenyl)-5 (2-aminoethoxycarbonyl)-1,4-dihydropyridine as a yellow solid. 1H-NMR (CDCl3); δ 1.85 (s, 2H); 2.40 (d, 6H); 3.40 (t, 2H); 3.68 (s, 3 H); 4.35 (s, 2H); 5.15 (s, 1H); 5.90 (s, 1H); 7.40 (t, 1H) 7.68 (d, 1H); 8.03 (d, 1H); 8.13 (s, 1H).

後処理

  1. temperatureat reflux for 2 hr
  2. additionis added
  3. temperaturethe mixture refluxed for an additional hr
  4. temperatureAfter cooling
  5. filtrationthe precipitate is collected by filtration
  6. washwashed with ethanol
  7. customthe filtrate evaporated under vacuum
  8. customto leave a yellow solid
  9. washwashed twice with 0.5N KOH, once with water
  10. dry with materialdried (MgSO4)
  11. filtrationfiltered
  12. customthe solvent removed under vacuum

出典と根拠

ORDレコード
ord-d005d79cc282482bb83da4ff22c94ce1
出典データセット
uspto-grants-1993_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05258519

反応ノート

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