p-Toluenesulfonic acid → 2-Pentenoic acid, 3-(3-pyridinylamino)-, methyl ester, (Z)-

HRID 893618Notes

Reaction equation

HRID 893618 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.C[CH2:9][CH2:10][C:11]([CH2:13][C:14]([O-:16])=[O:15])=O.[C:17]1(C)C=CC(S(O)(=O)=O)=CC=1>CCOCC>[CH3:17][O:16][C:14](=[O:15])/[CH:13]=[C:11](\[NH:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1)/[CH2:10][CH3:9]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 100093-AminopyridineHCID 119662643-Oxohexanoate

Product 1

HCID 198908032-Pentenoic acid, 3-(3-pyridinylamino)-, methyl ester, (Z)-Yield 467.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 3-aminopyridine (5.0 g), methylpropionylacetate (7.6 g) and p-toluenesulphonic acid (0.5 g) was stirred for 96 hours and then ether (100 ml) was added. The solution was washed with water (100 ml) and dried (MgSO4). The solvent was removed by evaporation and the residue purified by flash chromatography, eluting with ethyl acetate to give methyl-(Z)-3-(3-pyridylamino)-2-pentenoate (B3) (2.8 g) as an oil; NMR (CDCl3): 1.1(t,3H), 2.5(q,2H), 3.7(s,3H), 4.95(s,1H), 7.3(m,1H), 7.4(m,1H), 8.4(m,2H), 10.3(br,1H).

Workup

  1. washThe solution was washed with water (100 ml)
  2. dry with materialdried (MgSO4)
  3. customThe solvent was removed by evaporation
  4. customthe residue purified by flash chromatography
  5. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-d221c66ba92248faba65111fab6dcb1d
Source dataset
uspto-grants-1992_06
Patent number
US05126344

Reaction notes

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