Ethyl Acetate → Methyl 5-(pyrrol-1-yl)-3-pyridinecarboxylate

HRID 399802ノート

反応式

HRID 399802 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[N:6][CH:7]=1.CO[CH:14]1[CH2:18][CH2:17][CH:16](OC)O1.C(OCC)(=O)C.C(=O)([O-])[O-].[K+].[K+]>C(O)(=O)C.O>[N:1]1([C:2]2[CH:3]=[C:4]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[N:6][CH:7]=2)[CH:14]=[CH:18][CH:17]=[CH:16]1

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 790982,5-DimethoxytetrahydrofuranHCID 1514432Methyl 5-aminopyridine-3-carboxylate

生成物 1

HCID 18945279Methyl 5-(pyrrol-1-yl)-3-pyridinecarboxylate収率 57.1%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 962Water溶媒

実験手順

A mixture of methyl 5-amino-3-pyridinecarboxylate (1.7 g) and 2.5-dimethoxytetrahydrofuran (2.2 g) in acetic acid (5 ml) was refluxed for 30 minutes. After being cooled to room temperature, the reaction mixture was poured into a mixture of ethyl acetate (50 ml) and water (50 ml) under stirring, and adjusted to pH 8.5 with 10% potassium carbonate aqueous solution. The organic layer was washed with brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was recrystallized from diethyl ether-n-hexane to afford methyl 5-(pyrrol-1-yl)-3-pyridinecarboxylate (1.29 g).

後処理

  1. temperaturewas refluxed for 30 minutes
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated in vacuo
  5. customthe residue was recrystallized from diethyl ether-n-hexane

出典と根拠

ORDレコード
ord-293309cc602b4c708dcc6beba7efb024
出典データセット
uspto-grants-1998_10
特許番号
US05824691

反応ノート

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