Ammonium Hydroxide → HCID 11644588, compound

HRID 1872623Notes

Reaction equation

HRID 1872623 reaction equation
[N+]([O-])([O-])=O.[K+].[CH2:6]([C:9]1[S:10][C:11]2[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N:14]=[C:13]([NH2:21])[C:12]=2[N:22]=1)[CH2:7][CH3:8].[OH-].[NH4+:24]>S(=O)(=O)(O)O>[CH2:6]([C:9]1[S:10][C:11]2[C:20]3[CH:19]=[C:18]([NH2:24])[CH:17]=[CH:16][C:15]=3[N:14]=[C:13]([NH2:21])[C:12]=2[N:22]=1)[CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 24434Potassium NitrateHCID 101987192-propylthiazolo[4,5-c]quinolin-4-amine

Product 1

HCID 11644588HCID 11644588, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Potassium nitrate (0.46 g, 4.52 mmol) was added to a solution of 2-propylthiazolo[4,5-c]quinolin-4-amine (1 g, 4.11 mmol, Example 12) in sulfuric acid (10 mL). The reaction mixture was stirred at ambient temperature for 30 minutes, then poured onto ice, neutralized (pH=7) with ammonium hydroxide (150 mL) and then extracted with dichloromethane. The extract was washed with sodium bicarbonate, dried over magnesium sulfate and then concentrated under vacuum to provide 1 g of a yellow solid. This material was recrystallized from isopropanol/water to provide 0.84 g of 8-nitro-2-propylthiazolo[4,5-c]quinoline as a yellow solid, m.p. 228-230° C. Analysis: Calculated for C13H12N4O2S: % C, 54.15; % H, 4.20; % N, 19.43; Found: % C, 54.22; % H, 4.05; % N, 19.04.

Workup

  1. additionpoured onto ice
  2. extractionextracted with dichloromethane
  3. washThe extract was washed with sodium bicarbonate
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-e869170703c6413b875ce0a5af20d69d
Source dataset
uspto-grants-2000_08
Patent number
US06110929

Reaction notes

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