2-Butyrylamino-4-methyl-3-nitropyridine → 7-Methyl-2-propyl-1H-imidazo[4,5-b]pyridine

HRID 248399

Reaction equation

[C:1]([NH:6][C:7]1[C:12]([N+:13]([O-])=O)=[C:11]([CH3:16])[CH:10]=[CH:9][N:8]=1)(=O)[CH2:2][CH2:3][CH3:4]>C(O)(=O)C.C(O)C.[Fe]>[CH3:16][C:11]1[CH:10]=[CH:9][N:8]=[C:7]2[NH:6][C:1]([CH2:2][CH2:3][CH3:4])=[N:13][C:12]=12

Participants

Conditions

Temperature: 90 °C

Procedure

A solution of 2-butyrylamino-4-methyl-3-nitropyridine (7.0 g) and iron powder (17.5 g) in a mixture of acetic acid (14 ml) and ethanol (100 ml) was stirred at 90° C. for 3 hours under nitrogen atmosphere. After being cooled to room temperature, the reaction mixture was filtered through Celite and the filtrate was evaporated in vacuo. Ethyl acetate and saturated aqueous sodium hydrogencarbonate were added to the residue until pH 7~8 and the resulting suspension was filtered through Celite. The organic layer of the filtrate was separated, washed with brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was purified with silica gel column chromatography (eluent:ethyl acetate) to give 7-methyl-2-propyl-3H-imidazo[4,5-b]pyridine (3.6 g).

Workup

temperatureAfter being cooled to room temperature
filtrationthe reaction mixture was filtered through Celite
customthe filtrate was evaporated in vacuo
additionEthyl acetate and saturated aqueous sodium hydrogencarbonate were added to the residue until pH 7~8
filtrationthe resulting suspension was filtered through Celite
customThe organic layer of the filtrate was separated
washwashed with brine
dry with materialdried over magnesium sulfate
customThe solvent was evaporated in vacuo
customthe residue was purified with silica gel column chromatography (eluent:ethyl acetate)

Sources & evidence

ORD record: ord-4da3aa9301f2452fb4f12336cc0f127f
Source dataset: uspto-grants-1993_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05210092

Linked notes

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