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

HRID 893618

반응식

HRID 893618 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-d221c66ba92248faba65111fab6dcb1d
출처 데이터셋
uspto-grants-1992_06
특허 번호
US05126344

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