Isopropanol → Methyl 2-(morpholin-4-yl)pyridine-4-carboxylate

HRID 1838249ノート

反応式

HRID 1838249 の反応式
Cl[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([OH:7])=[O:6].[NH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.[CH:17](O)(C)C>>[O:14]1[CH2:15][CH2:16][N:11]([C:2]2[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=2)[C:5]([O:7][CH3:17])=[O:6])[CH2:12][CH2:13]1

参加物

4

反応物 3

HCID 3776IsopropanolHCID 8083MorpholineHCID 2369852-Chloroisonicotinic acid

生成物 1

HCID 2762487Methyl 2-(morpholin-4-yl)pyridine-4-carboxylate

反応条件

温度
150 °C

実験手順

A 5.0 g portion of 2-chloroisonicotinic acid and 6.91 g of morpholine were suspended in 16 ml of isopropanol and stirred at 150° C. for 27 hours in a sealed tube. The solvent was evaporated and then the residue was mixed with 70 ml of methanol and 5 ml of concentrated sulfuric acid and heated under reflux for 6.5 hours. The solvent was evaporated and the residue was dissolved in chloroform and washed with saturated aqueous sodium bicarbonate. After evaporation of the solvent, the resulting mixture was subjected to a silica gel column chromatography and eluted with hexane-ethyl acetate (4:1, v/v) to obtain 4.42 g of crystals of the title compound.

後処理

  1. customThe solvent was evaporated
  2. additionthe residue was mixed with 70 ml of methanol and 5 ml of concentrated sulfuric acid
  3. temperatureheated
  4. temperatureunder reflux for 6.5 hours
  5. customThe solvent was evaporated
  6. dissolutionthe residue was dissolved in chloroform
  7. washwashed with saturated aqueous sodium bicarbonate
  8. customAfter evaporation of the solvent
  9. washeluted with hexane-ethyl acetate (4:1

出典と根拠

ORDレコード
ord-1374b52180f84e949afd156745550029
出典データセット
uspto-grants-2004_01
特許番号
US06673799B1

反応ノート

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