Dimethylformamide → HCID 178515417, compound

HRID 636582Notes

Reaction equation

HRID 636582 reaction equation
[CH3:1][C:2]1[N:6]([C:7]2[N:17]=[CH:16][CH:15]=[CH:14][C:8]=2[C:9](OCC)=[O:10])[N:5]=[N:4][N:3]=1.CN(C)C=O.[O-]CC.[K+]>C(O)(=O)C>[N:5]1[N:6]2[C:7]3[C:8]([C:9]([OH:10])=[CH:1][C:2]2=[N:3][N:4]=1)=[CH:14][CH:15]=[CH:16][N:17]=3

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 12132861ethyl 2-(5-methyl-1H-tetrazol-1-yl)nicotinateHCID 23670592Potassium ethoxide

Product 1

HCID 178515417HCID 178515417, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Ethyl 2-(5-methyl-1H-tetrazol-1-yl)nicotinate (6.3 g, 27 mmole) was covered with N,N-dimethylformamide (50 mL), potassium ethoxide (4.5 g, 54 mmole) was added and the reaction mixture was stirred at ambient temperature for 2 hours. The reaction mixture was poured into ice water containing about 17 mL of acetic acid. The resulting precipitate was isolated by filtration, washed with water then dried to provide 4.5 g of tetrazolo[1,5-a][1,8]naphthyridin-5-ol as an off white solid, m.p. 236° (decomposition). Analysis: Calculated for C8H5N5O: % C, 51.34; % H, 2.69; % N, 37.42; Found: % C, 51.23; % H, 2.77; % N, 37.25.

Workup

  1. additionwas added
  2. customThe resulting precipitate was isolated by filtration
  3. washwashed with water
  4. customthen dried

Sources & evidence

ORD record
ord-55537cde97d64364b197bcf7899c17e0
Source dataset
uspto-grants-2001_02
Patent number
US06194425B1

Reaction notes

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