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CAS No. : | 64834-58-8 | MDL No. : | MFCD05863670 |
Formula : | C9H12ClNO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 185.65 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Class: | ||
Precautionary Statements: | UN#: | ||
Hazard Statements: | Packing Group: |
* 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 |
---|---|---|
25% | Stage #1: at 185℃; for 23 h; Stage #2: With hydrogenchloride In isopropyl alcohol |
To the mixture of 20 (10.00 g, 45.05 mmol) and ammonium chloride (1.76 g, 32.9 mmol), aluminum chloride (11.60 g, 87.02 mmol) was added at 185 °C. After 40 min and 70 min, further portions of aluminum chloride (5.80 g, 43.5 mmol and 11.60 g, 87.02 mmol) were added and the mixture was stirred for further 23 h at the same temperature. It was poured into a slurry of ice and 3 M HCl solution under strong agitation. The resulting solution was basified (pH 14) with 40percent NaOH and extracted with diethyl ether (300 mL and 2 * 150 mL). The organic layer was dried (MgSO4), and evaporated resulting in an oily residue (7.07 g, 94percent) containing the two isomers 19 and 27 in a ratio of 9: 1 as determined by GC-MS. It was dissolved in isopropyl alcohol (50 mL) and a solution of hydrochloric acid gas in isopropyl alcohol was added dropwise. The precipitate was filtered off. The residue was recrystallized twice from isopropyl alcohol to afford the title compound (2.32 g, 25percent) as a pale brown solid. Mp 244-246 °C (isopropyl alcohol, off-white solid). IR (KBr): ν = 3423, 1587, 1468 cm-1. 1H NMR (400 MHz, CD3OD): δ = 7.37 (br d, J = 7.7 Hz, 1H), 7.31 (t, J = 7.7 Hz, 1H), 7.24 (br d, J = 7.7 Hz, 1H), 4.37 (s, 2H), 3.49 (t, J = 6.3 Hz, 2H), 3.14 (br t, J = 6.3 Hz, 2H). 13C NMR (100 MHz, CD3OD): δ = 135.6, 133.3, 130.2, 129.0, 128.8, 127.3, 43.9, 42.2, 26.2. HRMS calcd. for C9H11ClN+ ([M+H]+): 168.0575, found: 168.0580. |