Acetic Acid → Diethyl 1,4-dihydro-4-(2'-ethoxy-3',5'-dinitro-6'-pentadecylphenyl)-2,6-dimethyl-3,5-pyridine dicarboxylate

HRID 1768125Notes

Reaction equation

HRID 1768125 reaction equation
[CH2:1]([O:3][C:4]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:9]([N+:15]([O-:17])=[O:16])=[C:8]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[C:5]=1[CH:6]=O)[CH3:2].[C:33]([O:39][CH2:40][CH3:41])(=[O:38])[CH2:34][C:35]([CH3:37])=O.C(O)(=O)C.N1CCCCC1.[CH3:52][CH2:53][O:54][C:55](/[CH:57]=[C:58](\[NH2:60])/[CH3:59])=[O:56]>C(O)CCC>[CH2:1]([O:3][C:4]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:9]([N+:15]([O-:17])=[O:16])=[C:8]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[C:5]=1[CH:6]1[C:34]([C:33]([O:39][CH2:40][CH3:41])=[O:38])=[C:35]([CH3:37])[NH:60][C:58]([CH3:59])=[C:57]1[C:55]([O:54][CH2:53][CH3:52])=[O:56])[CH3:2]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 8082PiperidineHCID 8868Ethyl AcetoacetateHCID 6437562-Butenoic acid, 3-amino-, ethyl ester, (2Z)-HCID 225745722-Ethoxy-3,5-dinitro-6-pentadecyl benzaldehyde

Product 1

HCID 10175604Diethyl 1,4-dihydro-4-(2'-ethoxy-3',5'-dinitro-6'-pentadecylphenyl)-2,6-dimethyl-3,5-pyridine dicarboxylate

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

2-Ethoxy-3,5-dinitro-6-pentadecyl benzaldehyde (3.73 g, 8.3 mmol) and ethyl acetoacetate (1.08 g, 8.3 mmol) were dissolved in n-butanol (20 mL). Acetic acid (0.5 g, 8.3 mmol) and piperidine (0.7 g, 8.3 mmol) were added and stirred at room temperature for 3-4 hrs. Ethyl-3-amino crotonate (1.08 g, 8.3 mmol) was then added and refluxed for 10 hrs. n-Butanol was evaporated and reaction mixture was washed with distilled water and extracted with dichloromethane (10 mL). Organic layer was dried over sodium sulfate, evaporated and compound was purified by column chromatography using silicagel (100-200 mesh) with hexane:EtOAc (94:6) solvent system to give diethyl 1,4-dihydro-4-(2′-ethoxy-3′,5′-dinitro-6′-pentadecylphenyl)-2,6-dimethyl-3,5-pyridine dicarboxylate.

Workup

  1. temperaturerefluxed for 10 hrs
  2. customn-Butanol was evaporated
  3. customreaction mixture
  4. washwas washed with distilled water
  5. extractionextracted with dichloromethane (10 mL)
  6. dry with materialOrganic layer was dried over sodium sulfate
  7. customevaporated
  8. customcompound was purified by column chromatography

Sources & evidence

ORD record
ord-873da836b0254d83a0eb6c5ce9d574ea
Source dataset
uspto-grants-2007_06
Patent number
US07235570B2

Reaction notes

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