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

HRID 415526Notes

Reaction equation

[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](Cl)=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=[N:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[NH2:23][CH2:24][CH2:25][CH2:26][OH:27]>CN(C=O)C>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:23][CH2:24][CH2:25][CH2:26][OH:27])=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a round-bottomed flask containing 7-bromo-4-chloro-3-nitroquinoline (60 g, 209.1 mmol) was added DMF (390 mL) and triethylamine (44 mL, 313.6 mmol) and the solution was stirred at 0° C. in an ice-bath. To this cooled solution was added 3-aminopropan-1-ol (17.6 mL, 230.0 mmol) and the reaction was stirred at ambient temperature overnight. The solvent was removed under reduced pressure and the resultant orange solid was recrystallized from ethyl acetate (800 mL). The product was separated by filtration and the solids were washed with diethyl ether and dried under reduced pressure to afford crude 3-[(7-bromo-3-nitroquinolin-4-yl)amino]propan-1-ol (88.15 g) as a brown solid.

Workup

stirringthe reaction was stirred at ambient temperature overnight
customThe solvent was removed under reduced pressure
customthe resultant orange solid was recrystallized from ethyl acetate (800 mL)
customThe product was separated by filtration
washthe solids were washed with diethyl ether
customdried under reduced pressure

Sources & evidence

ORD record: ord-e30229a339e04112b68726aaf712bbc4
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088788B2

Reaction notes

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