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CAS No. : | 30529-70-5 | MDL No. : | MFCD00134165 |
Formula : | C7H6ClNO2 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | ACQXHCHKMFYDPM-UHFFFAOYSA-N |
M.W : | 171.58 | Pubchem ID : | 121724 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With trichlorophosphate; | Reference Example 6 The preparation of 2-chloro-6-methylnicotinic acid Phosphorus oxychloride (50 ml) was added with cooling (icebath) to <strong>[38116-61-9]2-hydroxy-6-methylnicotinic acid</strong> (10 g) over a period of 20 minutes. The resulting suspension was stirred at the reflux temperature for 4 hours to give an orange solution. The excess phosphorus oxychloride was removed by evaporation. The residue was added carefully to ice/water with stirring. The mixture was basified to pH 10 with 2N sodium hydroxide solution then stirred for 1 hour. The resulting solution was washed with diethyl ether then acidified to pH 3-4 with concentrated hydrochloric acid. The mixture was extracted with ethyl acetate. The organic extracts were combined, dried and evaporated to yield the title compound as a yellow solid, 4.63 g, m.p. 161-162 C. Further acidification of the aqueous residue to pH 2 followed by extraction with ethyl acetate as described above yielded a further batch of the title compound as a cream solid, 5.81 g, m.p. 162-163 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In trichlorophosphate; | EXAMPLE 2 1-Ethyl-1,2-dihydro-4-hydroxy-7-methyl-2-oxo-1,8-naphthyridine-3-carboxylic acid ethyl ester A stirred mixture of 12 g. of <strong>[38116-61-9]2-hydroxy-6-methylnicotinic acid</strong> in 100 ml. of phosphorus oxychloride was heated under reflux for 3 hours. The phosphorus oxychloride was removed in a rotary evaporator and the residue was poured onto 500 ml. of ice. The mixture was stirred at room temperature for 3 hours and was filtered. The filter cake was collected, air dried and was recrystallized from ethyl acetate to give 7.0 g. of 2-chloro-6-methylnicotinic acid, m.p. 158-60 C. (Ref. Zalay et al., U.S. Pat. No. 3,838,120; m.p. 142-9 C. |
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