Pentanoic Acid → 2-butyl-1H-imidazo[4,5-b]pyridine

HRID 1029548Notes

Reaction equation

HRID 1029548 reaction equation
[C:1](O)(=O)[CH2:2][CH2:3][CH2:4][CH3:5].[NH2:8][C:9]1[C:14]([NH2:15])=[CH:13][CH:12]=[CH:11][N:10]=1>>[CH2:2]([C:1]1[NH:15][C:14]2[C:9]([N:8]=1)=[N:10][CH:11]=[CH:12][CH:13]=2)[CH2:3][CH2:4][CH3:5]

Participants

3

Reactant 2

HCID 7991Pentanoic AcidHCID 99562,3-Diaminopyridine

Product 1

HCID 124677102-butyl-1H-imidazo[4,5-b]pyridineYield 95%

Conditions

Temperature
100 °C

Procedure

A mixture of valeric acid (5.50 mL, 50.4 mmol), 2,3-diaminopyridine (5.0 g, 45.8 mmol), and polyphosphoric acid (50 g) was heated to 100° C. with stirring for 5 hours. Basification (NH4OH), extraction (EtOAc, 4×20 mL), drying (K2CO3), and concentration gave 7.61 g (95%) of the title compound as an amorphous tan solid which was judged pure by 1H NMR and tlc (mp ca 80° C. without recrystallization).

Workup

  1. extractionBasification (NH4OH), extraction (EtOAc, 4×20 mL)
  2. customdrying
  3. concentration(K2CO3), and concentration

Sources & evidence

ORD record
ord-df0433d777ec4f05bae29a39b98b1403
Source dataset
uspto-grants-1992_04
Patent number
US05102880

Reaction notes

Loading…