Acetic Acid → HCID 11820506, compound

HRID 728115Notes

Reaction equation

HRID 728115 reaction equation
[CH3:1][C:2]1[C:3]([CH:8]=[CH:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.C(O)(=O)C.[H][H]>C(O)C.O1CCCC1.[Pd]>[CH3:1][C:2]1[C:3]([CH2:8][CH2:9][C:10]2[CH:11]=[CH:12][C:13]([NH2:16])=[CH:14][CH:15]=2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 53948724HCID 53948724, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 11820506HCID 11820506, compoundYield 91.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-methyl-2-[2-(4-nitrophenyl)vinyl]pyridine (13.0 g) in ethanol (250 ml), tetrahydrofuran 250 ml) and acetic acid (13 ml) was hydrogenated over 10% palladium on carbon (3 g) under atmospheric pressure of hydrogen gas for 7 hours at ambient temperature. The catalyst was removed by filtration and the filtrate was evaporated in vacuo. The residue was dissolved in a mixture of ethyl acetate and water and the resultant solution was adjusted to pH 7.0 with aqueous 20% potassium carbonate. The separated organic layer was washed with brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was crystallized from diethyl ether and diisopropyl ether to give 3-methyl-2-[2-(4-aminophenyl)ethyl]pyridine (10.5 g).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was evaporated in vacuo
  3. dissolutionThe residue was dissolved in a mixture of ethyl acetate and water
  4. washThe separated organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated in vacuo
  7. customthe residue was crystallized from diethyl ether and diisopropyl ether

Sources & evidence

ORD record
ord-16a4a3ba252b4c77b3ceabced66b39ef
Source dataset
uspto-grants-1991_09
Patent number
US05047411

Reaction notes

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