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

HRID 47459

Reaction equation

HRID 47459 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-e2660c48de33439390b2a581508cb241
Source dataset
uspto-grants-2004_03
Patent number
US06699878B2

Linked notes

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