Dimethylformamide → HCID 178526937, compound

HRID 47460

Reaction equation

HRID 47460 reaction equation
[O-:1]CC.[K+].[CH3:5][C:6]1[N:10]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][C:16]=2[C:17]([O:19]CC)=O)[N:9]=[N:8][N:7]=1.CN(C)C=O>C(O)(=O)C>[OH2:1].[N:9]1[N:10]2[C:11]3[C:16]([C:17]([OH:19])=[CH:5][C:6]2=[N:7][N:8]=1)=[CH:15][CH:14]=[N:13][CH:12]=3

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 22172739ethyl 3-(5-methyl-1H-tetrazol-1-yl)pyridine-4-carboxylateHCID 23670592Potassium ethoxide

Product 1

HCID 178526937HCID 178526937, compoundYield 90.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Potassium ethoxide (20.2 g) was added to a mixture of ethyl 3-(5-methyl-1H-tetrazol-1-yl)pyridine-4-carboxylate (28 g) and dimethylformamide (280 mL). The reaction mixture was allowed to stir at ambient temperature overnight then poured into cold dilute acetic acid. The resulting precipitate was collected, washed with water and dried to provide 22.4 g of tetrazolo[1,5-a][1,7]naphthyridin-5-ol hydrate as a solid, m.p. 247-248° C. (decomposition). Analysis: Calculated for C8H5N5O: %C, 46.83; %H, 3.44; %N, 34.13. Found: %C, 46.48; %H, 3.42; %N, 34.03.

Workup

  1. customThe resulting precipitate was collected
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-bd0cdde275de498d9a53580003c5b510
Source dataset
uspto-grants-2004_03
Patent number
US06699878B2

Linked notes

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