Triethylamine → (7-Bromo-3-nitroquinolin-yl)(4,4-dimethoxybutyl)amine

HRID 1623129Notes

Reaction equation

[CH3:1][O:2][CH:3]([O:8][CH3:9])[CH2:4][CH2:5][CH2:6][NH2:7].C(N(CC)CC)C.C(=O)([O-])[O-].[K+].[K+].[Br:23][C:24]1[CH:33]=[C:32]2[C:27]([C:28](Cl)=[C:29]([N+:34]([O-:36])=[O:35])[CH:30]=[N:31]2)=[CH:26][CH:25]=1>C(Cl)(Cl)Cl.O>[Br:23][C:24]1[CH:33]=[C:32]2[C:27]([CH:28]=[C:29]([N+:34]([O-:36])=[O:35])[C:30]([NH:7][CH2:6][CH2:5][CH2:4][CH:3]([O:8][CH3:9])[O:2][CH3:1])=[N:31]2)=[CH:26][CH:25]=1

Participants

Conditions

Temperature: 0 °C

Procedure

4-Aminobutyraldehyde dimethylacetal (29.41 g, 208.6 mmol), triethylamine (36.36 mL), and potassium carbonate (24.0 g, 173.9 mmol) were added sequentially to a solution of 7-bromo-4-chloro-3-nitroquinoline (50.1 g, 173.9 mmol) in chloroform (200 mL) cooled to 0° C. The reaction was allowed to warm to ambient temperature and was stirred for 4 hours. The reaction mixture was then diluted with water (100 mL) and the reaction was stirred for 10 minutes and the layers were separated. The organic layer was washed with saturated aqueous sodium bicarbonate and brine, dried over magnesium sulfate, and concentrated under reduced pressure to afford 66.9 g of (7-bromo-3-nitroquinolin-yl)(4,4-dimethoxybutyl)amine as a yellow solid.

Workup

temperatureto warm to ambient temperature
stirringthe reaction was stirred for 10 minutes
customthe layers were separated
washThe organic layer was washed with saturated aqueous sodium bicarbonate and brine
dry with materialdried over magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-0669756bf596497f8eb2d4a3b8581c7d
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778963B2

Reaction notes

Loading…