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ChemicalBook CAS DataBase List QUINOLINE-5,6-DIAMINE
42143-23-7

QUINOLINE-5,6-DIAMINE synthesis

7synthesis methods
-

Yield:42143-23-7 89%

Reaction Conditions:

with hydrogen;palladium 10% on activated carbon in ethanol; for 2 h;

Steps:

10.A

To a solution of 50% palladium on carbon (10% wet, 250 mg) in absolute ethanol(100 mL) under nitrogen atmosphere, was added 5-amino-6-nitroquinoHne (5.00 g, 26.4 mmol). With stirring, the solution was placed in vacuo for 30 seconds and then was put under H2 atmosphere using a hydrogen gas-filled balloon. The reaction was allowed to stir for 2 hours, then the reaction flask was evacuated in vacuo and placed under nitrogen atmosphere. The reaction mixture- was then sonicated for 10 minutes and methanol (50 mL) was added. The resulting solution was then placed under H2 atmosphere again and allowedL to stir for 2 hours. After evacuating the flask of hydrogen, the reaction mixture was filtered through a Celite pad and the pad was washed with methanol (2 χ 200 mL). The combined filtrate and washings were concentrated in vacuo and the resulting residue was dissolved in CH2C12 (75 mL). The resulting solution was purified using an IS CO 330-g Redi-Sep column (0-10% methanoI/CH2Cl2 as eluent) to provide Compound Int-lOa as a yellow solid (3.76 g, 89%).

References:

WO2011/87740,2011,A1 Location in patent:Page/Page column 79; 80

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