Hydrochloric Acid → HCID 178419866, compound

HRID 1862034Notes

Reaction equation

HRID 1862034 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 (5 mL 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-b0a2fe649cd047feb9e7ed3de35dc081
Source dataset
uspto-grants-2003_03
Patent number
US06534654B2

Reaction notes

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