Acetone → 2-Methyl-[(4-nitro-5-tetrazolo[1,5-a]quinolinyl)amino]-2-propanol

HRID 2182762Notes

Reaction equation

HRID 2182762 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[CH3:5][C:6]([OH:24])([CH3:23])[CH2:7][NH:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[C:11](Cl)[C:10]=1[N+:20]([O-:22])=[O:21].CN(C)C=O.CC(C)=O>O>[CH3:23][C:6]([OH:24])([CH3:5])[CH2:7][NH:8][C:9]1[C:18]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:1]2[N:2]=[N:3][N:12]=[C:11]2[C:10]=1[N+:20]([O-:22])=[O:21]

Participants

6

Reactant 4

HCID 180Acetone2×HCID 6228DimethylformamideHCID 33557Sodium AzideHCID 120516961-((2-Chloro-3-nitroquinolin-4-yl)amino)-2-methylpropan-2-ol

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium Azide (19.5 g, 0.3 moles), 2-methyl-[(2-chloro-3-nitroquinolin-4-yl)amino]-2-propanol (29.6 g, 0.10 mole, U.S. Pat. No. 4,988,815 Example 12) and N,N-dimethylformamide (100 mL) were added to a jacketed 1 liter round bottom flask with the outside portion containing acetone. The reaction mixture was stirred with a stirring bar and the acetone refluxed to provide a constant internal reaction temperature of 53° C. After 18 hours the reaction mixture was diluted with water (100 mL). The resulting yellow precipitate was isolated by filtration then washed with 50% N,N-dimethylformamide/water until the washes became light colored. The yellow/green solid was then washed with water, pressed dry and washed with ether. The solid was air dried to provide 27.2 g of crude product as a yellow/light green solid. This material was recrystallized from ethanol/dichloromethane to provide 2-methyl-[(4-nitro-5-tetrazolo[1,5-a]quinolinyl)amino]-2-propanol as a yellow crystalline solid, m.p. 204° C. (dec.). Analysis: Calculated for: C13H14N6O3: % C, 51.65; % H, 4.67; % N, 27.8; Found: % C, 51.30; % H, 4.69; % N, 27.43.

Workup

  1. customto provide a constant internal reaction temperature of 53° C
  2. customThe resulting yellow precipitate was isolated by filtration
  3. washthen washed with 50% N,N-dimethylformamide/water until the washes
  4. washThe yellow/green solid was then washed with water
  5. custompressed dry
  6. washwashed with ether
  7. customdried
  8. customto provide 27.2 g of crude product as a yellow/light green solid
  9. customThis material was recrystallized from ethanol/dichloromethane

Sources & evidence

ORD record
ord-9f9bd523eb5f4d53a842dd6253fc2a30
Source dataset
uspto-grants-2005_05
Patent number
US06897314B2

Reaction notes

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