Hydrochloric Acid → HCID 178419866, compound

HRID 2182772Notes

Reaction equation

HRID 2182772 reaction equation
CC([N:5]1[C:17]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]3[N:18]=[N:19][N:20]=[C:9]3[C:8]=2[N:7]=[CH:6]1)(C)C.Cl.[OH-].[Na+]>O>[N:18]1[N:10]2[C:11]3[C:16]([C:17]4[NH:5][CH:6]=[N:7][C:8]=4[C:9]2=[N:20][N:19]=1)=[CH:15][CH:14]=[CH:13][CH:12]=3

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 12114565HCID 12114565, compound

Product 1

HCID 178419866HCID 178419866, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6-(1,1-Dimethylethyl)-6H-imidazo[4,5-c]tetrazolo[1,5-a]quinoline (1 g, 3.8 mmole, Example 20) was added to hydrochloric acid (5mL of 6N); water (20 mL) was added and the mixture was heated on a steam bath for 1 hour. The reaction mixture was allowed to cool to ambient temperature then made basic (pH 11) by the addition of sodium hydroxide solution. The resulting precipitate was isolated by filtration, dried then recrystallized from N,N-dimethylformamide to provide 0.65 g of the desired product as a solid. A sample of this material was refluxed in a large amount of dichloromethane/methanol, isolated by filtration, then dried to provide 6H-imidazo[4,5-c]tetrazolo[1,5-a]quinoline as a solid, m.p. >300° C. Analysis: Calculated for C10H6N6: % C, 57.14; % H, 2.88; % N, 39.98; Found: % C, 56.89; % H, 3.10; % N 39.34. The structure was confirmed by both mass spectroscopy and nuclear magnetic resonance spectroscopy.

Workup

  1. temperaturethe mixture was heated on a steam bath for 1 hour
  2. customThe resulting precipitate was isolated by filtration
  3. customdried
  4. customthen recrystallized from N,N-dimethylformamide

Sources & evidence

ORD record
ord-583705d375bc4806a9e17a6558766081
Source dataset
uspto-grants-2005_05
Patent number
US06897314B2

Reaction notes

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