Sodium Hydroxide → HCID 178526872, compound

HRID 1795402Notes

Reaction equation

HRID 1795402 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 began 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 C9H5N5O3: % 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-3052eb55ce864689a3bfc2a2fbb569a2
Source dataset
uspto-grants-2006_04
Patent number
US07026482B2

Reaction notes

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