Sodium Hydroxide → HCID 178526872, compound

HRID 1168569Notes

Reaction equation

HRID 1168569 reaction equation
[OH-:1].[Na+].CC(O)(C)CN[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]2[N:17]=[N:18][N:19]=[C:9]2[C:8]=1[N+:20]([O-:22])=[O:21]>O>[N+:20]([C:8]1[C:9]2[N:10]([N:17]=[N:18][N:19]=2)[C:11]2[C:16]([C:7]=1[OH:1])=[CH:15][CH:14]=[CH:13][CH:12]=2)([O-:22])=[O:21]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 154897582-Methyl-[(4-nitro-5-tetrazolo[1,5-a]quinolinyl)amino]-2-propanol

Product 1

HCID 178526872HCID 178526872, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Aqueous sodium hydroxide (30 g of 50%) was added to a suspension of 2-methyl-[(4-nitro-5-tetrazolo[1,5-a]quinolinyl)amino]-2-propanol (34.0 g, 0.1125 mole, Example 3) in water (500 mL). The mixture was heated on a steam bath and the solid dissolved rapidly. The solution was heated for about 30 minutes and then upon stirring a solid begin to precipitate. The mixture was made acidic with 6N hydrochloric acid. The resulting solid was isolated by filtration; washed in succession with water, ethanol and ether; then dried under vacuum at 100° C. to provide 23.2 g of crude product as a pale yellow/green solid. A sample (3.2 g) was recrystallized initially from methanol/dichloromethane and then from toluene to provide 4-nitrotetrazolo[1,5-a]quinolin-5-ol. Analysis: Calculated for C9H5H5O3: %C, 46.76; %H, 2.18; %N, 30.29; Found: %C, 46.85; %H, 2.23; %N, 29.91.

Workup

  1. temperatureThe mixture was heated on a steam bath
  2. dissolutionthe solid dissolved rapidly
  3. temperatureThe solution was heated for about 30 minutes
  4. customto precipitate
  5. customThe resulting solid was isolated by filtration
  6. washwashed in succession with water, ethanol and ether
  7. customthen dried under vacuum at 100° C.
  8. customto provide 23.2 g of crude product as a pale yellow/green solid
  9. customA sample (3.2 g) was recrystallized initially from methanol/dichloromethane

Sources & evidence

ORD record
ord-ff50a8e12d8f4b8391b2f45f6786d13a
Source dataset
uspto-grants-2003_09
Patent number
US06624305B2

Reaction notes

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