ChemicalBook CAS DataBase List QUINOLINE-5,6-DIAMINE

QUINOLINE-5,6-DIAMINE synthesis

7synthesis methods

Product Name:QUINOLINE-5,6-DIAMINE
CAS Number:42143-23-7
Molecular formula:C9H9N3
Molecular Weight:159.19

35975-00-9 Synthesis

35975-00-9
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$15.88/Price $/250mgs:

42143-23-7
33 suppliers
$160.00/100mg

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