8-Aminoquinoline → N-(1-phenylethyl)quinolin-8-amine

HRID 41319

Reaction equation

[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.Br[CH:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:14]>C(N(CC)CC)C>[C:15]1([CH:13]([NH:1][C:2]2[CH:3]=[CH:4][CH:5]=[C:6]3[C:11]=2[N:10]=[CH:9][CH:8]=[CH:7]3)[CH3:14])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 1.44 g (10.0 mmol) of 8-aminoquinoline, 1.01 g (10.0 mmol) of triethylamine and 1.85 g (10.0 mmol) of 1-bromo-1-phenylethane (1) was stirred for 2 hr at 120° C. One more portion of 1.01 g of triethylamine as well as 1.85 g of 1-bromo-1-phenylethane was added. The resulting mixture was stirred for additional 2 hr at 120° C. One more portion of triethylamine and 1-bromo-1-phenylethane was added, and the reaction mixture was stirred for 2 hr at 120° C. Finally, the product was isolated using flash chromatography on silica gel 60 (40-63 um, eluent: hexanes-ethyl acetate=20:1, vol.) to give 2.26 g (91%) of the title compound.

Workup

stirringThe resulting mixture was stirred for additional 2 hr at 120° C
stirringthe reaction mixture was stirred for 2 hr at 120° C
customFinally, the product was isolated

Sources & evidence

ORD record: ord-5de44a545cb64177b7b1ef6fdc63fc77
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08530593B2

Linked notes

Loading…