Isopropanol → Isopropyl 6-chloronicotinate

HRID 746509노트

반응식

HRID 746509 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 23512700Isopropyl 6-chloronicotinate수율 114%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e327f254940645bbb299a79d53d0ca65
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07393859B2

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