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ChemicalBook CAS DataBase List 4-METHYL-1,2,3,4-TETRAHYDRO-ISOQUINOLINE HYDROCHLORIDE
111661-47-3

4-METHYL-1,2,3,4-TETRAHYDRO-ISOQUINOLINE HYDROCHLORIDE synthesis

1synthesis methods
4-Methylisoquinoline

1196-39-0

4-METHYL-1,2,3,4-TETRAHYDRO-ISOQUINOLINE HYDROCHLORIDE

111661-47-3

General procedure for the synthesis of 4-methyl-1,2,3,4-tetrahydroisoquinoline hydrochloride from 4-methylisoquinoline: 0.50 g (3.5 mmol) of 4-methylisoquinoline was dissolved in 50 mL of methanol under a hydrogen atmosphere, and the hydrogenation reaction was carried out with the addition of 50 mg of dichloromethane and 3.5 mL of aqueous 1 M hydrochloric acid. Upon completion of the reaction, the catalyst was removed by diafiltration followed by evaporation of the reaction mixture. A mixture containing the starting material and the product was obtained, which could be used directly in the next step of the reaction without further purification. The yield was 0.60 g, which represents 94% of the theoretical yield.ESI-MS detection showed: m/z = 148 ([M + H]+).

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Yield:111661-47-3 94%

Reaction Conditions:

with hydrogenchloride;hydrogen;platinum(IV) oxide in methanol at 20; under 2250.23 Torr; for 4 h;

Steps:

69

4-methyl-1,2,3,4-tetrahydro-isoquinolin hydrochloride In a hydrogen atmosphere 0.50 g (3.5 mmol) 4-methyl-isoquinoline, 50 mg platinum dioxide in 50 mL methanol and 3.5 mL 1M aqueous hydrochloric acid solution were hydrogenated at RT and 3 bar for 4 h. After removal of the catalyst by suction filtering the reaction mixture was evaporated down. A mixture of educt and product was obtained, which was reacted further without any further purification. Yield: 0.60 g (94% of theory) ESI-MS: m/z=148 (M+H)+

References:

US2011/195954,2011,A1 Location in patent:Page/Page column 104-105