Bicarbonate Ion → 2-Chloro-4,6-dimethylpyridine

HRID 880468ノート

反応式

HRID 880468 の反応式
N[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[N:3]=1.[Cl-:10].[Na+].N([O-])=O.[Na+].C(=O)(O)[O-]>Cl.O>[Cl:10][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[N:3]=1

参加物

7

反応物 4

HCID 769Bicarbonate IonHCID 5234Sodium Chloride2 回HCID 215072-Amino-4,6-dimethylpyridineHCID 23668193Sodium Nitrite

生成物 1

HCID 125083782-Chloro-4,6-dimethylpyridine収率 38.4%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 962Water溶媒

実験手順

A mixture of 2-amino-4,6-dimethylpyridine (90 g, 0.736 mol) and sodium chloride (216 g, 3.69 mol) in concentrated hydrochloric acid (720 mL) was cooled to between −15 and −20° C. A solution of sodium nitrite (71.2 g, 1.03 mol) in water (135 mL) was added over 30 min. More sodium chloride (216 g, 3.69 mol) was added and the reaction mixture was allowed to warm to ambient temperature and stirred for 1 h. The reaction mixture was basified with solid bicarbonate (700 g) and extracted with dichloromethane (1 L), filtered and the two phases separated. The organic layer was concentrated in vacuo and the crude purified by flash column chromatography over silica gel (100-200 mesh) with 20% dichloromethane in petroleum ether as eluent to afford 2-chloro-4,6-dimethylpyridine (40 g, 38%) as a solid.

後処理

  1. temperaturewas cooled to between −15 and −20° C
  2. extractionextracted with dichloromethane (1 L)
  3. filtrationfiltered
  4. customthe two phases separated
  5. concentrationThe organic layer was concentrated in vacuo
  6. customthe crude purified by flash column chromatography over silica gel (100-200 mesh) with 20% dichloromethane in petroleum ether as eluent

出典と根拠

ORDレコード
ord-954cae20cb8e47b4afe63beaa3c037ca
出典データセット
uspto-grants-2015_03
特許番号
US08993574B2

反応ノート

読み込み中…