2-Chloronicotinic acid → 2-(2-Methylpropoxy)pyridine-3-carboxylic acid

HRID 354161ノート

反応式

HRID 354161 の反応式
[Na].Cl[C:3]1[N:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=[O:6]>C(O)C(C)C>[CH2:5]([O:6][C:3]1[N:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=[O:6])[CH:4]([CH3:8])[CH3:3]

参加物

4

反応物 2

HCID 762582-Chloronicotinic acidHCID 5360545Sodium

生成物 1

HCID 235115682-(2-Methylpropoxy)pyridine-3-carboxylic acid収率 168.1%

試薬・触媒・溶媒 1

HCID 6560Isobutanol溶媒2 回

反応条件

温度
80 °C

実験手順

Sodium metal (3 g, 0.127 mol) was added in small amounts to isobutanol (100 mL)—some warming (80° C.) was needed to facilitate dissolution. 2-Chloronicotinic acid (10 g, 0.064 mol) was added and the solution refluxed for 1 h. A thick mixture resulted and a further 100 mL isobutanol was added and the mixture refluxed for 3 h. The mixture was cooled and quenched with 2N hydrochloric acid. The product was extracted into ethyl acetate and the organics washed with dilute hydrochloric acid (pH 3), dried (MgSO4) and concentrated to give a brown solid. Purification by flash column chromatography (ethyl acetate as eluant) gave 10.5 g of product as a yellow solid.

後処理

  1. dissolutiondissolution
  2. temperaturethe solution refluxed for 1 h
  3. customA thick mixture resulted
  4. temperaturethe mixture refluxed for 3 h
  5. temperatureThe mixture was cooled
  6. customquenched with 2N hydrochloric acid
  7. extractionThe product was extracted into ethyl acetate
  8. washthe organics washed with dilute hydrochloric acid (pH 3)
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated
  11. customto give a brown solid
  12. customPurification by flash column chromatography (ethyl acetate as eluant)

出典と根拠

ORDレコード
ord-017b6a9dc9654a8cb6db2f40c208bcf4
出典データセット
uspto-grants-2004_06
特許番号
US06756373B1

反応ノート

読み込み中…