Ammonia → HCID 178437486, compound

HRID 1779440Notes

Reaction equation

HRID 1779440 reaction equation
[CH2:1]([C:3]1[NH:13][C:6]2=[N:7][C:8]([CH3:12])=[CH:9][C:10]([CH3:11])=[C:5]2[N:4]=1)[CH3:2].S(=O)(=O)(O)O.[N+:19]([O-])([O-:21])=[O:20].[K+].N>>[CH2:1]([C:3]1[NH:13][C:6]2=[N:7][C:8]([CH3:12])=[C:9]([N+:19]([O-:21])=[O:20])[C:10]([CH3:11])=[C:5]2[N:4]=1)[CH3:2]

Participants

5

Reactant 4

HCID 222AmmoniaHCID 1118Sulfuric AcidHCID 24434Potassium NitrateHCID 178437439HCID 178437439, compound

Product 1

HCID 178437486HCID 178437486, compoundYield 37%

Conditions

Temperature
80 °C

Procedure

2-Ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridine (2.17 g) was added to stirred fuming sulphuric acid (7 ml) and the resulting solution was warmed to 80° C. Potassium nitrate (3.0 g) was added in portions over a period of 10 minutes and the resulting mixture was heated am between 95 and 100° C. for 10 minutes, cooled, then poured onto ice (approx. 25 g). The mixture was neutralised with concentrated aqueous ammonia solution and then extracted with dichloromethane (2×50 ml). The combined extracts were dried over magnesium sulphate and the solvent was then evaporated. Recrystallization of the resulting residue from ethyl acetate (15 ml) gave the intermediate compound 2-ethyl-5,7-dimethyl-6-nitro-3H-imidazo-[4,5-b]pyridine (1.01 g; m.p. 146°-149° C.).

Workup

  1. temperaturethe resulting mixture was heated am between 95 and 100° C. for 10 minutes
  2. temperaturecooled
  3. additionpoured onto ice (approx. 25 g)
  4. extractionextracted with dichloromethane (2×50 ml)
  5. dry with materialThe combined extracts were dried over magnesium sulphate
  6. customthe solvent was then evaporated
  7. customRecrystallization of the resulting residue from ethyl acetate (15 ml)

Sources & evidence

ORD record
ord-8b0ae94ba3b147e9b0956e1d4d45f89b
Source dataset
uspto-grants-1997_05
Patent number
US05627191

Reaction notes

Loading…