HCID 19772188, compound → HCID 19772209, compound

HRID 1614668Notes

Reaction equation

HRID 1614668 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6](/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][O:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]3[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=3)[N:13]=2)[CH:7]=[CH:8][CH:9]=1)([O-])=O>CO>[NH2:1][C:4]1[CH:5]=[C:6](/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][O:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]3[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=3)[N:13]=2)[CH:7]=[CH:8][CH:9]=1

Participants

3

Reactant 1

HCID 19772188HCID 19772188, compound

Product 1

HCID 19772209HCID 19772209, compoundYield 84.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To 1.6 g of 2-[(E)-2-(3-nitrophenyl)ethenyl]-6-[4-(4-methylphenyl)butoxy]methylpyridine was added 10 ml of methanol and then added 3 g of stannous chloride dihydride in 10 ml of methanol, and the mixture was stirred under reflux for 3.5 hours. After completion of the reaction, the solvent was distilled off and the residue was made alkaline with an aqueous sodium hydroxide solution. To the solution was added ethyl acetate and the mixture was filtered by sellaite. The organic layer was separated, washed with water, and dried over anhydrous magnesium sulfate and then the solvent was distilled off to give 1.6 g of a crude oily substance. The crude oily substance was purified on chromatography by passing chloroform and then a mixture of chloroform and ethanol(50:1) to give 1.25 g of 2-[(E)-2-(3-aminophenyl)ethenyl]-6-[4-(4-methylphenyl) butoxy]methylpyridine as an oily substance.

Workup

  1. temperatureunder reflux for 3.5 hours
  2. customAfter completion of the reaction
  3. distillationthe solvent was distilled off
  4. additionTo the solution was added ethyl acetate
  5. filtrationthe mixture was filtered by sellaite
  6. customThe organic layer was separated
  7. washwashed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationthe solvent was distilled off
  10. customto give 1.6 g of a crude oily substance
  11. customThe crude oily substance was purified on chromatography
  12. additiona mixture of chloroform and ethanol(50:1)

Sources & evidence

ORD record
ord-d7e0f48b6118473e8350e0cc1e290349
Source dataset
uspto-grants-1993_03
Patent number
US05198452

Reaction notes

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