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CAS No. : | 26673-30-3 | MDL No. : | MFCD08544416 |
Formula : | C10H9ClO | Boiling Point : | 306.2°C at 760 mmHg |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 180.63 g/mol | Pubchem ID : | 12206522 |
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: |
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Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | Stage #1: With hydrogenchloride; sodium nitrite In ethanol; water at 0℃; for 0.25 h; Stage #2: With copper(l) chloride In ethanol; water at 95℃; for 0.25 h; |
5-amino-3,4-dihydronaphthalen-l(2H)-one (1 g, 6.2 mmol) in HCl (36percent, 2 mL) and EtOH (8 mL) at 0 °C was treated with an aqueous solution of NaN02 (0.582 g, 8.4 mmol in 1 mL water for 15 min. This mixture was added to a solution of CuCl (0.3 g, 3.1 mmol) in HCl (36percent, 10 mL) at 95 °C and kept at this temperature for 15 min. The solution was cooled down to room temperature, diluted with water, and extracted with EtOAc. The organic phase was collected, washed with sat. NaHCC , dried over MgSC , and purified by column chromatography with 40-50percent EtOAc:Hex on silica gel. Desired compound was afforded. (0.7 g, 62percent). NMR (400 MHz, chloroform-d) δ 7.53 (dd, / = 7.8, 1.2 Hz, 1H), 7.14 (tt, / = 7.8, 0.7 Hz, 1H), 6.88 (dd, / = 7.8, 1.2 Hz, 1H), 3.70 (s, 2H), 2.69 (t, / = 6.2 Hz, 2H), 2.66 - 2.60 (m, 2H), 2.30 - 2.07 (m, 2H). |
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