Hydrochloric Acid → Ethyl 6-hydroxynicotinate

HRID 2080004ノート

反応式

HRID 2080004 の反応式
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.Cl.C(=O)(O)[O-].[Na+].[CH2:17](O)[CH3:18]>>[CH2:17]([O:7][C:6]([C:5]1[CH:9]=[CH:10][C:2](=[O:1])[NH:3][CH:4]=1)=[O:8])[CH3:18]

参加物

5

反応物 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 516892Sodium BicarbonateHCID 178418479HCID 178418479、化合物

生成物 1

HCID 295861Ethyl 6-hydroxynicotinate収率 65%

反応条件

温度
110 °C

実験手順

To a suspension of 6-hydroxy-nicotinic acid (5.00 g, 35.9 mmol) in ethanol (60 mL) was added 1N hydrochloric acid (20 mL), which was then stirred at 110° C. for 3 hours. The reaction solution was cooled to 0° C., then, an aqueous solution of saturated sodium bicarbonate was added, the solution was extracted with ethyl acetate and tetrahydrofuran, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo, the residue was purified by silica gel column chromatography (ethyl acetate), and the title compound (3.90 g, 23.3 mmol, 65%) was obtained as a white solid.

後処理

  1. temperatureThe reaction solution was cooled to 0° C.
  2. extractionthe solution was extracted with ethyl acetate and tetrahydrofuran
  3. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated in vacuo
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate)

出典と根拠

ORDレコード
ord-f3786a8e0e5d4e75956a0988b796ee80
出典データセット
uspto-grants-2011_04
特許番号
US07932272B2

反応ノート

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