Dimethylformamide → HCID 178526937, compound

HRID 2120792Notes

Reaction equation

HRID 2120792 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-c0c78a94821a40719dd1d94181e88682
Source dataset
uspto-grants-2004_02
Patent number
US06693113B2

Reaction notes

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