Nitric Acid → HCID 178526970, compound

HRID 2304792Notes

Reaction equation

HRID 2304792 reaction equation
[N:1]1[N:5]2[C:6]3[C:11]([C:12]([OH:14])=[CH:13][C:4]2=[N:3][N:2]=1)=[CH:10][CH:9]=[CH:8][CH:7]=3.[N+:15]([O-])([OH:17])=[O:16]>C(O)(=O)C>[OH2:14].[N+:15]([C:13]1[C:4]2[N:5]([N:1]=[N:2][N:3]=2)[C:6]2[C:11]([C:12]=1[OH:14])=[CH:10][CH:9]=[CH:8][CH:7]=2)([O-:17])=[O:16]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 178515414HCID 178515414, compound

Product 1

HCID 178526970HCID 178526970, compoundYield 120.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
40 °C

Procedure

Tetrazolo[1,5-a]quinolin-5-ol (10 g, 54 mmole, Example 1) was suspended in acetic acid (200 mL) then warmed to 40° C. Nitric acid (4 mL of 16M, 59 mmole) was added to the reaction mixture. The reaction mixture was heated at 80° C. for 30 minutes then allowed to cool to ambient temperature. The resulting precipitate was isolated by filtration, rinsed with water then recrystallized from isopropanol/water to provide 8.1 g of 4-nitrotetrazolo[1,5-a]quinolin-5-ol hydrate as light yellow plates, m.p. 186.5-187° C. Analysis: Calculated for C9H5N5O3. H2O: %C, 43.38; %H, 2.83; %N, 28.10; Found: %C, 43.27; %H, 2.84; %N, 28.25.

Workup

  1. temperatureThe reaction mixture was heated at 80° C. for 30 minutes
  2. temperatureto cool to ambient temperature
  3. customThe resulting precipitate was isolated by filtration
  4. washrinsed with water
  5. customthen recrystallized from isopropanol/water

Sources & evidence

ORD record
ord-7c6a34d8fbe849819f940a82a9d5ddf9
Source dataset
uspto-grants-2002_08
Patent number
US06437131B1

Reaction notes

Loading…