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CAS No. : | 7652-29-1 | MDL No. : | MFCD00174511 |
Formula : | C8H6ClNO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | OBPIPKQQNRACHV-UHFFFAOYSA-N |
M.W : | 183.59 | Pubchem ID : | 309259 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
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 |
---|---|---|
62% | In 1-methyl-pyrrolidin-2-one; at 250℃; for 20h; | A suspension of commercially available 6-chloro-4H-benzo[1,4]oxazin-3-one (1.83 g) and copper(I) cyanide (1.81 g) in N-methyl-pyrrolidin-2-one (40 mL) was placed in a preheated oil bath (250 C.). After stirring at this temperature for 20 h, the mixture was cooled to room temperature, diluted with water (200 mL) and extracted with ethyl acetate (3×200 mL). The combined organic layers were washed with water (2×200 mL) and brine (200 mL), dried (MgSO4), filtered and concentrated. The remaining residue was purified by flash chromatography (silica, cyclohexane/ethyl acetate) to afford the title compound (1.08 g; 62%). [MH]+=175. |
24% | In N-methyl-pirrolidine-2-one; at 250℃; | A suspension of commercially available 6-chloro-4H-benzo[l,4]oxazin-3-one (3.2 g) and CuCN (2.9 g) in dry N-methyl-pyrrolidin-2-one (15 mL) was placed in a preheated oil bath (~250C). After stirring at this temperature overnight, the mixture was concentrated, diluted with H2O (200 mL) and extracted with EtOAc (3 x 200 mL). The combined organic layers were washed with H2O (2 x 200 mL) and saturated aqueous NaCl (200 mL), dried (MgSO4), filtered and concentrated. The remaining residue crystallized from EtOAc/toluene to afford the title compound as a tan solid (720 mg, 24%). [MH]+ = 175. |
24% | In 1-methyl-pyrrolidin-2-one; at 250℃; | Preparative Example 6; Step A; A solution of commercially available 6-chloro-4H-benzo[1,4]oxazin-3-one (3.2 g) and CuCN (2.9 g) in anhydrous N-methylpyrrolidone (15 mL) was stirred overnight in a pressure tube at 250 C. and then evaporated under reduced pressure. The residue was diluted with ethyl acetate, filtered and the remaining liquid was washed subsequently with 10% citric acid, saturated sodium hydrogen carbonate and brine, dried (MgSO4) and concentrated. Crystallization from toluene/ethyl acetate afforded the intermediate (720 mg; 24%) as a tan solid. [MH]+=175. |
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