Isopropanol → Isopropyl 6-chloronicotinate

HRID 1280487ノート

反応式

HRID 1280487 の反応式
[C:1]([C:8]1NC=CN=1)([C:3]1NC=CN=1)=O.[Cl:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[CH:16][N:15]=1.C(O)(C)C>ClCCl>[Cl:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([O:20][CH:1]([CH3:8])[CH3:3])=[O:19])=[CH:16][N:15]=1

参加物

5

反応物 3

HCID 3776IsopropanolHCID 792226-Chloronicotinic acidHCID 5250894Bis-(1H-imidazol-2-YL)-methanone

生成物 1

HCID 23512700Isopropyl 6-chloronicotinate収率 114%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Carbonyl diimidazole (18.6 g, 0.115 mol) was added to a suspension of 6-chloronicotinic acid (16.6 g, 0.105 mol) in dichloromethane (250 mL). After all of the solid had dissolved the reaction solution was stirred at ambient temperature for 1 hour and then isopropyl alcohol (100 mL) was added. The dichloromethane was removed under vacuum. A catalytic amount of sodium isopropoxide was added to the solution and the solution was heated at reflux for 1 hour. The solution was then concentrated under vacuum. The resulting residue was slurried with water and then extracted with diethyl ether. The extract was dried over magnesium sulfate and then concentrated under vacuum to provide 23.9 g of isopropyl 6-chloronicotinate.

後処理

  1. dissolutionAfter all of the solid had dissolved the reaction solution
  2. customThe dichloromethane was removed under vacuum
  3. additionA catalytic amount of sodium isopropoxide was added to the solution
  4. temperaturethe solution was heated
  5. temperatureat reflux for 1 hour
  6. concentrationThe solution was then concentrated under vacuum
  7. extractionextracted with diethyl ether
  8. dry with materialThe extract was dried over magnesium sulfate
  9. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-27dc14fa44864eaf82a921795298dbb9
出典データセット
uspto-grants-2002_09
特許番号
US06451810B1

反応ノート

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