Dimethylformamide diethylacetal → ethyl 3-(5-methyl-1H-tetrazol-1-yl)pyridine-4-carboxylate

HRID 1168351Notes

Reaction equation

HRID 1168351 reaction equation
C([O:3][CH:4]([O:8][CH2:9][CH3:10])N(C)C)C.[CH3:11][C:12]1[N:16]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][C:22]=2C(O)=O)[N:15]=[N:14][N:13]=1>ClCCl>[CH3:11][C:12]1[N:16]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][C:22]=2[C:4]([O:8][CH2:9][CH3:10])=[O:3])[N:15]=[N:14][N:13]=1

Participants

4

Reactant 2

HCID 70913Dimethylformamide diethylacetalHCID 221726643-(5-methyl-1H-tetrazol-1-yl)pyridine-4-carboxylic acid

Product 1

HCID 22172739ethyl 3-(5-methyl-1H-tetrazol-1-yl)pyridine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dimethylformamide diethyl acetal (46 mL) was added to a suspension of 3-(5-methyl-1H-tetrazol-1-yl)pyridine-4-carboxylic acid (36 g) in dichloromethane (800 mL). The reaction mixture was stirred at ambient temperature overnight then washed six times with water (500 mL), dried over magnesium sulfated, and concentrated under vacuum. The residue was recrystallized from ethyl acetate/hexanes to provide 40 g of ethyl 3-(5-methyl-1H-tetrazol-1-yl)pyridine-4-carboxylate as a solid.

Workup

  1. washthen washed six times with water (500 mL)
  2. dry with materialdried over magnesium
  3. concentrationconcentrated under vacuum
  4. customThe residue was recrystallized from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-9cdfd6adc71946049d907eb349a00ae8
Source dataset
uspto-grants-2003_09
Patent number
US06624172B2

Reaction notes

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