Hydrochloric Acid → HCID 178437448, compound

HRID 1779442Notes

Reaction equation

HRID 1779442 reaction equation
N[C:2]1[C:3]([CH3:14])=[C:4]2[N:11]=[C:10]([CH2:12][CH3:13])[NH:9][C:5]2=[N:6][C:7]=1[CH3:8].N([O-])=O.[Na+].[ClH:19]>O>[ClH:19].[Cl:19][C:2]1[C:3]([CH3:14])=[C:4]2[N:11]=[C:10]([CH2:12][CH3:13])[NH:9][C:5]2=[N:6][C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 23668193Sodium NitriteHCID 178437484HCID 178437484, compound

Product 1

HCID 178437448HCID 178437448, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

6-Amino-2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]-pyridine (0.85 g; preparable as in Example 10(b)) was dissolved with stirring in a mixture of concentrated hydrochloric acid (1.15 ml) and water (1.15 ml) and the resulting solution was cooled to 0° C. A solution of sodium nitrite (0.34 g) in water (1 ml) was added, dropwise, keeping the internal temperature below 5° C. The resulting solution was stirred at this temperature for 10 minutes and then added to a stirred solution of cuprous chloride (0.48 g) in concentrated hydrochloric acid (t.7 ml) keeping the temperature below 10° C. The mixture obtained was stirred at 70° C. for 2 hours and then cooled to ambient temperature. A precipitate was collected and washed with water (5 ml). Recrystallisation of this precipitate from methanol (7.5 ml) gave the intermediate compound 6-chloro-2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridine hydrochloride (0.21 g; m.p. 284°-287° C. with decomposition). When left for 18 hours the reaction mixture yielded a further quantity of precipitate, which was collected by filtration and recrystallised from methanol to give a second crop (70 mg) of the intermediate compound identified above.

Workup

  1. customthe internal temperature below 5° C
  2. customthe temperature below 10° C
  3. customThe mixture obtained
  4. stirringwas stirred at 70° C. for 2 hours
  5. temperaturecooled to ambient temperature
  6. customA precipitate was collected
  7. washwashed with water (5 ml)
  8. customRecrystallisation of this precipitate from methanol (7.5 ml)

Sources & evidence

ORD record
ord-07c0174362d84c8989810876bf30cd76
Source dataset
uspto-grants-1997_05
Patent number
US05627191

Reaction notes

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