methyl [1-(2-chlorophenyl)-5-hydroxy-1H-pyrazol-3-yl]acetate synthesis
- Product Name:methyl [1-(2-chlorophenyl)-5-hydroxy-1H-pyrazol-3-yl]acetate
- CAS Number:1158233-60-3
- Molecular formula:C12H11ClN2O3
- Molecular Weight:266.68
Yield:1158233-60-3 61%
Reaction Conditions:
with N-ethyl-N,N-diisopropylamine in toluene at 130 - 140; for 48 h;
Steps:
1.a
Example 1: Formation of 2-(2-chlorophenyl)-4-methyl-5-(2-morpholin-4-ylbenzyl)-1H-pyrazolor[4,3-c]pyridine-3,6(2H,5H)-dione (1)(Compound Ia, Scheme 1); [Show Image] a) methyl [1-(2-chlorophenyl)-5-hydroxy-1H-pyrazol-3-yl]acetate (Compound of Formula (IV), Scheme 1).; To a suspension of 2-chlorophenylhydrazine (1.82 g, 10.16 mmol, 1 equiv.) in anhydrous toluene (50 ml) were added successively diisopropylethylamine (2.1 ml, 12.19 mmol, 1.2 equiv.) and dimethyl 3-oxopentanedioate (1.77 g, 10.16 mmol, 1 equiv.). The resulting mixture was heated at 130-140 °C using a Dean-Stark apparatus (some wet toluene was allowed to distill off). After 2 h, the hydrazone intermediate was cleanly formed. Additional diisopropylethylamine (2.1 ml, 12.19 mmol, 1.2 equiv.) was then added and the resulting mixture heated at 140 °C for 46 h using Dean-Stark system. Most of the remaining hydrazone can be removed by washings of the crude mixture with toluene. The resulting brown oil was purified by flash chromatography over SiO2. 1.65 g of pure methyl [1-(2-chlorophenyl)-5-hydroxy-1H-pyrazol-3-yl]acetate was obtained as a yellowish solid. Yield 61%. MS(ESI+): 267.8; MS(ESI-): 265.6.
References:
EP2166010,2010,A1 Location in patent:Page/Page column 25
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