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

HRID 2372714
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HRID 2372714 반응식
[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]
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참가 물질

6

반응물 3

HCID 9321HydrazineHCID 24654Hydrazine hydrate (1:1)HCID 137998311,4-Dihydro-2,6-dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-5-(2-phthalimidoethoxy)carbonyl-pyridine

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol
용매
HCID 6344Dichloromethane용매

실험 절차

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 0.5 N 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-dihydropyridi ne as a yellow solid. 1H-NMR (CDCl3); δ 1.85 (s, 2H); 2.40 (d, 6H); 3.40 (t, 2H); 3.68 (s, 3H); 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).

후처리

  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 0.5 N KOH, once with water
  10. dry with materialdried (MgSO4)
  11. filtrationfiltered
  12. customthe solvent removed under vacuum

출처 및 근거

ORD 기록
ord-f256ddd092e0417e9dc22dfc649090a0
출처 데이터셋
uspto-grants-1992_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05100892

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