2-CHLORO-5,6,7,8-TETRAHYDROQUINOLINE 1-OXIDE synthesis
- Product Name:2-CHLORO-5,6,7,8-TETRAHYDROQUINOLINE 1-OXIDE
- CAS Number:130861-71-1
- Molecular formula:C9H10ClNO
- Molecular Weight:183.63
21172-88-3
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Yield:-
Reaction Conditions:
with sodium tungstate (VI) dihydrate;dihydrogen peroxide in acetic acid; for 4 h;Heating;Concentration;Time;
Steps:
2-Chlorotetrahydroquinoline N-Oxide (7) (Step 4)
To a 1000 mL four-necked jacketed flask fitted with a mechanical stirrer, an addition funnel, a thermometer, and a condenser were added 2-chlorotetrahydroquinoline (5; 83.5 g, 0.5 mol, 1 equiv), Na2WO4·2H2O (1.65 g, 1 mol%), and AcOH (200 mL). The resulting mixture was heated to 80 °C. H2O2 (30 wt%, 85.0 g) was slowly added over a period of 3 h, and an additional portion of 30% H2O2 (17.0 g) was added after 1 h. HPLC analysis of the crude mixture showed that the conversion of 2-chlorotetrahydroquinoline (5) was almost complete. The cooled reaction mixture was directly concentrated under reduced pressure, then AcOH (100 mL) was added and again concentrated. The operation was repeated twice to afford the crude N-oxide7 (108 g) as a brown oil and directly used in the next step.
References:
Zong, Zhijian;Wu, Ke;Jin, Liqun;Sun, Nan;Hu, Baoxiang;Shen, Zhenlu;Hu, Xinquan [Synthesis,2020,vol. 52,# 23,p. 3675 - 3683]
54802-19-6
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108-94-1
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4471-09-4
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85031-42-1
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