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

HRID 893618

反応式

HRID 893618 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d221c66ba92248faba65111fab6dcb1d
出典データセット
uspto-grants-1992_06
特許番号
US05126344

関連ノート

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