ChemicalBook CAS DataBase List 3,4-DIPHENYLISOQUINOLINE

3,4-DIPHENYLISOQUINOLINE synthesis

8synthesis methods

Product Name:3,4-DIPHENYLISOQUINOLINE
CAS Number:52839-45-9
Molecular formula:C21H15N
Molecular Weight:281.35

26260-02-6 Synthesis

26260-02-6
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501-65-5
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52839-45-9
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1801-42-9
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Yield:52839-45-9 91% ，1801-42-9 3%

Reaction Conditions:

Stage #1: 2-iodobenzaldehydewith tert-butylamine in N,N-dimethyl-formamide;Inert atmosphere;
Stage #2: diphenyl acetylenewith [Pd(η(5)-C5H5)Fe(η(5)-C5H3-C(CH3)=N-C6H4-4-CH3)Cl(P(C6H5)3)];sodium carbonate;lithium chloride in N,N-dimethyl-formamide at 100; for 24 h;Inert atmosphere;

Steps:

4.2. General procedure for synthesis of isoquinolines

General procedure: To a solution of o-halobenzaldehyde (0.25 mmol) in DMF (1 mL), tert-butyl amine (0.75 mmol) was added. The resulting mixture was stirred under a nitrogen atmosphere at room temperature for 12 h (or 100 °C for 4 h). After the haloaldehyde was consumed completely (monitored by TLC), alkynes (0.50 mmol), Na₂CO₃ (0.50 mmol), LiCl (0.25 mmol), palladacycle (1 mol %), and DMF (1 mL) were added to the mixture. Then the vial was placed in a preheated oil bath and heated at 100 °C under stirring for 24 h. After the reaction was complete (monitored by TLC), the mixture was diluted with CH₂Cl₂ (10 mL), filtered through a pad of Celite, and extracted with CH₂Cl₂. The combined organic phase was dried over anhydrous Na₂SO₄, filtered, and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel (ethyl acetate/hexane) to afford the pure product.

References:

Yang, Fan;Zhang, Junli;Wu, Yangjie [Tetrahedron,2011,vol. 67,# 16,p. 2969 - 2973] Location in patent:experimental part

501-65-5
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$16.00/5g