ChemicalBook CAS DataBase List IMIDAZO[1,2-A]PYRIDINE-6-CARBOXYLIC ACID

IMIDAZO[1,2-A]PYRIDINE-6-CARBOXYLIC ACID synthesis

9synthesis methods

Product Name:IMIDAZO[1,2-A]PYRIDINE-6-CARBOXYLIC ACID
CAS Number:139022-25-6
Molecular formula:C8H6N2O2
Molecular Weight:162.15

3167-49-5 Synthesis

3167-49-5
371 suppliers
$8.00/5g

97-97-2
292 suppliers
$24.00/25mL

IMIDAZO[1,2-A]PYRIDINE-6-CARBOXYLIC ACID

139022-25-6
162 suppliers
$10.00/250mg

Yield:139022-25-6 80.3 g

Reaction Conditions:

Stage #1: chloroacetaldehyde dimethyl acetalwith hydrogenchloride;water in ethanol at 25 - 85; for 1 h;
Stage #2: 6-aminonicotinic acid in ethanol;water at 85; for 24 h;

Steps:

1 Example 1: Preparation of imidazo[l,2-a]pyridine-6-carboxylic acid (IX):

A mixture of chloroacetaldehyde dimethylacetal (247.3 mL), 1M hydrochloric acid (800 mL) and ethanol (150 mL) was heated to 100 °C and stirred for 1 hour at the same temperature. The reaction mass was then cooled to 25 °C and its pH adjusted to 6.5-7.0 with solid sodium bicarbonate (68 g). 6-Amino nicotinic acid (100 g) was added to the above reaction mass in a portion wise manner at 25-30 °C. The reaction mass was slowly heated to 85 °C and stirred for 24 hours at the same temperature. The reaction mass was cooled to 0 °C and its pH adjusted to ~6 with a saturated solution of sodium bicarbonate. The resulting precipitate was filtered and dried at 40 °C for 4 hours to afford the title compound.Yield: 80.3 g

References:

WO2021/229605,2021,A1 Location in patent:Page/Page column 30