cas 21172-88-3, 2-chloro-5,6,7,8-tetrahydroquinoline | Articles data ｜lookchem

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21172-88-3

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Large-Scale Synthesis of 2-Chlorotetrahydroquinoline and 2-Chlorotetrahydroquinolin-8-one
An efficient large-scale preparation of 2-chlorotetrahydroquinoline with cyclohexanone and benzylamine as starting materials was developed and well optimized, in which benzyl-protected enamide was successfully cyclized and benzyl group was directly removed under Vilsmeier conditions. Azeotropic distillation provided 264 g of 2-chlorotetrahydroquinoline (79%) on a 2 mol scale of reaction without intermediate isolation. The downstream product 2-chlorotetrahydroquinolin-8-one was acquired through Boekelheide rearrangement, hydrolysis of acetate via NaBH 4reduction, and Anelli oxidation. With the developed procedure, the intermediates were not necessary to be isolated and 2-chlorotetrahydroquinolin-8-one was conveniently obtained with solvent slurry in 65% overall isolated yield in a four-step sequence.
Zong, Zhijian,Wu, Ke,Jin, Liqun,Sun, Nan,Hu, Baoxiang,Shen, Zhenlu,Hu, Xinquan
p. 3675 - 3683
(2020)
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More Articles about upstream products of 21172-88-3

130861-71-1
2-chloro-5,6,7,8-tetrahydroquinoline N-oxide

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Chemical Properties

Melting Point: 93-95 °C
Boiling Point: 260℃
Flash Point:136℃
Density: 1.185
Storage Temp.:under inert gas (nitrogen or Argon) at 2-8°C
PKA: 1.46±0.20(Predicted)
PSA: 12.89000
LogP: 2.61380

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