Hydrochloric Acid → 5-Amino-2-propylimidazo[4,5-b]pyridine

HRID 1029564Notes

Reaction equation

HRID 1029564 reaction equation
C([NH:6][C:7]1[N:12]=[C:11]2[N:13]=[C:14]([CH2:16][CH2:17][CH3:18])[NH:15][C:10]2=[CH:9][CH:8]=1)(=O)CCC.Cl>CO>[NH2:6][C:7]1[N:12]=[C:11]2[N:13]=[C:14]([CH2:16][CH2:17][CH3:18])[NH:15][C:10]2=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 224073815-Butyramido-2-propylimidazo[4,5-b]pyridine

Product 1

HCID 224075845-Amino-2-propylimidazo[4,5-b]pyridineYield 79.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
45 °C

Procedure

A mixture of 5-butyramido-2-propylimidazo[4,5-b]pyridine (250 mg, 1.07 mmol), MeOH (20 mL), and concentrated aqueous HCl (2 mL) was heated to 45° C. for 16 hours. Concentration and neutralization with NaHCO3 gave 150 mg of the title compound as a glass. 1H NMR (300 MHz, CD3OD) δ7.57 (d, 1H, J=8.5 Hz), 6.46 (d, 1H, J=8.5 Hz), 2.76 (t, 2H, J=7.5 Hz), 1.85-1.70 (m, 2H), 0.93 (t, 3H, J=7.5 Hz).

Workup

  1. concentrationConcentration and neutralization with NaHCO3

Sources & evidence

ORD record
ord-211dd52dad554c2ea62a6b4140159ddc
Source dataset
uspto-grants-1992_04
Patent number
US05102880

Reaction notes

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