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ChemicalBook CAS DataBase List Indoline
496-15-1

Indoline synthesis

13synthesis methods
Indolene is manufactured from (theoretically) 2 Mol. Indole plus 1 Mol. Hydroxycitronellal by condensation under heating. The proportions may vary slightly, and it is common practice to add Diethyl phthalate to the mixture prior to heating, so that the condensation product is somewhat protected against local overheating, and the finished product becomes light of color and fairly pourable at room temperature.
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Yield:496-15-1 99%

Reaction Conditions:

with hydrogen in water at 100; under 22502.3 Torr; for 10 h;

Steps:

3.2. Hydrogenation reaction in aqueous phase

General procedure: To showcase the applicability of this novel catalyst, the hydrogenationwas utilized for the other N-heterocyclic compounds. Asshown in Table 4, the hydrogenation of pyridine and 4-methylpyridinecould afford the desired product in excellent yield without by-products(Table 4, entries 1 and 2) although the reactivity of 4-methylpyridinewas somewhat less than that of pyridine, and a slightly longer reactiontime (7.5 h) was needed for full conversion (Table 4, entry 2). Additionally,indole was entirely transformed to dihydroindole and quinolinewas completely converted to 1,2,3,4-tetrahydroquinoline withhigh selectivity, respectively (Table 4, entries 3 and 4).

References:

Qian, Wei;Lin, Lina;Qiao, Yunxiang;Zhao;Xu, Zichen;Gong, Honghui;Li;Chen;Huang, Rong;Hou, Zhenshan [Applied Catalysis A: General,2019,vol. 585,art. no. 117183]

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