Triethylamine → N1-(3-nitroquinolin-1-yl)-2-methylpropane-1,2-diamine

HRID 1925461

Reaction equation

[NH2:1][CH2:2][C:3]([NH2:6])([CH3:5])[CH3:4].C(N(CC)CC)C.Cl[C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]=[CH:17][C:16]=1[N+:25]([O-:27])=[O:26]>ClCCl>[N+:25]([C:16]1[CH2:17][N:18]([NH:1][CH2:2][C:3]([CH3:5])([NH2:6])[CH3:4])[C:19]2[C:24]([CH:15]=1)=[CH:23][CH:22]=[CH:21][CH:20]=2)([O-:27])=[O:26]

Participants

Conditions

Temperature: 0 °C

Procedure

Under a nitrogen atmosphere, a solution of 1,2-diamino-2-methylpropane (52.20 mL, 503.3 mmol), triethylamine (131.8 mL, 958.8 mmol), and dichloromethane (1.0 L) was chilled in an ice water bath. 4-Chloro-3-nitroquinoline (100.0 g, 479.4 mmol) was added in portions over a period of 5 minutes. The reaction mixture was stirred at 0° C. for 2 hours and then allowed to slowly warm to ambient temperature. After 16 hours the reaction mixture was concentrated under reduced pressure. The residue was triturated with water (500 mL) for 1 hour. The resulting solid was isolated by filtration and dried overnight in a vacuum desiccator to provide 124.6 g of N1-(3-nitroquinolin-1-yl)-2-methylpropane-1,2-diamine as a yellow crystalline solid.

Workup

temperatureto slowly warm to ambient temperature
concentrationAfter 16 hours the reaction mixture was concentrated under reduced pressure
customThe residue was triturated with water (500 mL) for 1 hour
customThe resulting solid was isolated by filtration
customdried overnight in a vacuum desiccator

Sources & evidence

ORD record: ord-8a8989253b5349c0afd5f6e981c9a991
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178677B2

Linked notes

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