Iodoethane → ethyl 2-(5-methyl-1H-tetrazol-1-yl)nicotinate

HRID 1007769Notes

Reaction equation

HRID 1007769 reaction equation
[CH3:1][C:2]1[N:6]([C:7]2[N:15]=[CH:14][CH:13]=[CH:12][C:8]=2[C:9]([OH:11])=[O:10])[N:5]=[N:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:22](I)[CH3:23]>CC(C)=O>[CH3:1][C:2]1[N:6]([C:7]2[N:15]=[CH:14][CH:13]=[CH:12][C:8]=2[C:9]([O:11][CH2:22][CH3:23])=[O:10])[N:5]=[N:4][N:3]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 121328602-(5-Methyl-1H-tetrazol-1-yl)nicotinic acid

Product 1

HCID 12132861ethyl 2-(5-methyl-1H-tetrazol-1-yl)nicotinate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-(5-Methyl-1H-tetrazol-1-yl)nicotinic acid (5.6 g, 27 mmole) was suspended in acetone (250 mL), potassium carbonate (5 g) and ethyl iodide (5 mL) were added and the reaction mixture was heated at reflux for 2 hours. The acetone was removed under vacuum. The residue was partitioned between water and dichloromethane. The dichloromethane layer was separated, dried, then concentrated under vacuum to provide 6.3 g of ethyl 2-(5-methyl-1H-tetrazol-1-yl)nicotinate.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 2 hours
  3. customThe acetone was removed under vacuum
  4. customThe residue was partitioned between water and dichloromethane
  5. customThe dichloromethane layer was separated
  6. customdried
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-9779f5845f3c41919d31540df367e37e
Source dataset
uspto-grants-2004_09
Patent number
US06797716B2

Reaction notes

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