Hydrochloric Acid → 5-(3-Methyl-1,2,4-oxadiazol-5-yl)-3-pyridinecarboxylic acid

HRID 399800

反応式

HRID 399800 の反応式
[OH:1][N:2]=[C:3]([NH2:5])[CH3:4].[H-].[Na+].C[O:9][C:10]([C:12]1[CH:13]=[N:14][CH:15]=[C:16]([C:18](OC)=O)[CH:17]=1)=[O:11].Cl>O1CCCC1.O.C(OCC)(=O)C>[CH3:4][C:3]1[N:5]=[C:18]([C:16]2[CH:17]=[C:12]([C:10]([OH:11])=[O:9])[CH:13]=[N:14][CH:15]=2)[O:1][N:2]=1

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 30926N-HydroxyacetamidineHCID 78339Dimethyl pyridine-3,5-dicarboxylate

生成物 1

HCID 189454415-(3-Methyl-1,2,4-oxadiazol-5-yl)-3-pyridinecarboxylic acid収率 32%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a suspension of 1-(hydroxyimino)ethylamine (7.4 g) in dry tetrahydrofuran (450 ml) was added sodium hydride (3.7 g, 60% in mineral oil) carefully. The mixture was stirred at room temperature for 15 minutes, and refluxed for 30 minutes. To this mixture was added 3,5-bis(methoxycarbonyl)pyridine (15 g), and the mixture was refluxed for 3 hours. After being cooled to room temperature, the reaction mixture was poured into a mixture of ethyl acetate (200 ml) and water (200 ml) under stirring. The aqueous layer was adjusted to pH 3.5 with 10% hydrochloric acid. The resulting precipitate was collected by filtration, washed with water and dried in vacuo to afford 5-(3-methyl-1,2,4-oxadiazol-5-yl)-3-pyridinecarboxylic acid (5.04 g).

後処理

  1. temperaturerefluxed for 30 minutes
  2. temperaturethe mixture was refluxed for 3 hours
  3. temperatureAfter being cooled to room temperature
  4. stirringunder stirring
  5. filtrationThe resulting precipitate was collected by filtration
  6. washwashed with water
  7. customdried in vacuo

出典と根拠

ORDレコード
ord-10620e7650ea4b268785acb95674cca6
出典データセット
uspto-grants-1998_10
特許番号
US05824691

関連ノート

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