3-Aminobutan-1-ol → 3-[(7-Bromo-3-nitroquinolin-4-yl)amino]propan-1-ol

HRID 1187414Notes

Reaction equation

[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([N+:13]([O-:15])=[O:14])[C:8](Cl)=[N:9]2)=[CH:4][CH:3]=1.[NH2:16][CH:17](C)[CH2:18][CH2:19][OH:20]>ClCCl>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:16][CH2:17][CH2:18][CH2:19][OH:20])=[C:7]([N+:13]([O-:15])=[O:14])[CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 7-bromochloro-3-nitroquinoline (10.00 g, 34.78 mmol) in dichloromethane (140 mL) was added triethylanine (10.2 mL, 73.1 mmol). The solution was cooled to 0° C., and 3-amino-1-butanol (2.80 mL, 36.5 mmol) was added. The solution was stirred overnight at ambient temperature and then filtered to collect a precipitate. The precipitate was washed with dichloromethane and water. The filtrate was washed with saturated aqueous sodium bicarbonate and then added to the precipitate. The mixture was concentrated under reduced pressure. Methanol and toluene were added several times and removed under reduced pressure. The resulting solid was dried under high vacuum to provide 11.34 g of 3-[(7-bromo-3-nitroquinolin-4-yl)amino]propan-1-ol as a yellow solid.

Workup

filtrationfiltered
customto collect a precipitate
washThe precipitate was washed with dichloromethane and water
washThe filtrate was washed with saturated aqueous sodium bicarbonate
additionadded to the precipitate
concentrationThe mixture was concentrated under reduced pressure
additionMethanol and toluene were added several times
customremoved under reduced pressure
customThe resulting solid was dried under high vacuum

Sources & evidence

ORD record: ord-9b68e56957564099971895a949267d6f
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673932B2

Reaction notes

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