Isopropanol → Isopropyl 6-chloronicotinate

HRID 746509Notes

Reaction equation

HRID 746509 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 23512700Isopropyl 6-chloronicotinateYield 114%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-e327f254940645bbb299a79d53d0ca65
Source dataset
uspto-grants-2008_07
Patent number
US07393859B2

Reaction notes

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