Nitric Acid → HCID 178526970, compound

HRID 2182761Notes

Reaction equation

HRID 2182761 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-bfd49c7302f240d484cc69fd7568fd53
Source dataset
uspto-grants-2005_05
Patent number
US06897314B2

Reaction notes

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