1-(3-Methylpyridin-2-yl)ethan-1-one → 5-Chloro-2-(3-methylpyridin-2-yl)-1,8-naphthyridine

HRID 1724876ノート

反応式

HRID 1724876 の反応式
[NH2:1][C:2]1[N:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:3]=1[CH:4]=O.[C:11]([C:14]1[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][N:15]=1)(=O)[CH3:12].CC([O-])(C)C.[K+]>C1COCC1>[Cl:10][C:6]1[CH:7]=[CH:8][N:9]=[C:2]2[C:3]=1[CH:4]=[CH:12][C:11]([C:14]1[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][N:15]=1)=[N:1]2

参加物

5

反応物 3

HCID 130686691-(3-Methylpyridin-2-yl)ethan-1-oneHCID 23665647Potassium tert-butoxideHCID 462035412-Amino-4-chloropyridine-3-carbaldehyde

生成物 1

HCID 575610685-Chloro-2-(3-methylpyridin-2-yl)-1,8-naphthyridine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-20 °C

実験手順

Dissolve 2-amino-4-chloronicotinaldehyde (156 mg, 1.0 mmol) and 2-acetyl-3-methylpyridine (136 mg, 1.0 mmol) in anhydrous THF (5.0 mL) and cool it to −20° C. under N2 atmosphere. Add in portion t-BuOK (224 mg, 2.0 mmol) to the reaction mixture and stir the mixture at 110° C. for 2 hours. Concentrate the reaction mixture under vacuum, dilute the residue with water (10 mL), filter the solid, wash the solid with water and dry under high vacuum to afford the title product as a yellow colored solid.

後処理

  1. concentrationConcentrate the reaction mixture under vacuum
  2. additiondilute the residue with water (10 mL)
  3. filtrationfilter the solid
  4. washwash the solid with water
  5. customdry under high vacuum

出典と根拠

ORDレコード
ord-55a15a94dd2845c5881bd7d5b2d23bf3
出典データセット
uspto-grants-2009_02
特許番号
US07488740B2

反応ノート

読み込み中…