METHYL 3-HYDROXY-4-(1H-IMIDAZOL-2-YL)BENZOATE synthesis
- Product Name:METHYL 3-HYDROXY-4-(1H-IMIDAZOL-2-YL)BENZOATE
- CAS Number:1282516-54-4
- Molecular formula:C11H10N2O3
- Molecular Weight:218.21
Yield:1282516-54-4 71%
Reaction Conditions:
with ammonia in methanol;water; for 2 h;
Steps:
37
A mixture of methyl 4-formyl-3-hydroxybenzoate (4.8 g, 27 mmol), 40% aqueous solution of ethanedial (11.6 g, 79.93 mmol) and 50% aqueous ammonia (6.8 g, 399 mmol) in methanol (50 mL) was stirred for 2 hours or longer until the reaction is done. The solvent was removed by rotary evaporation, and the residue was partitioned between ethyl acetate and water. The mixture was filtered to remove the precipitates. pH was adjusted to 5-6 by careful addition of 1 N HCl. The aqueous layer was extracted with EtOAc three times. The combined organic layer was washed with water, brine and dried over MgSO4. The residue was purified by flash chromatography to yield methyl 3-hydroxy-4-(1H-imidazol-2-yl)benzoate as a yellow solid (4 g, 71%)
References:
US2012/245144,2012,A1 Location in patent:Page/Page column 105
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