8-Aminoquinoline → N-[(2-Methylphenyl)(phenyl)methyl]quinolin-8-amine

HRID 41323

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:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:20]>C(N(CC)CC)C>[CH3:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[CH:13]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[NH: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

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 4.75 g (33 mmol) of 8-aminoquinoline, 3.03 g (30 mmol) of triethylamine and 7.85 g (30 mmol) of 6 was stirred for 2 hr at 120° C. One more portion of 3.03 g of triethylamine as well as 7.85 g of 6 was added. The resulting mixture was stirred for additional 2 hr at 120° C. Next, one more portion of triethylamine and 6 were 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.). Yield 2.78 g (26%).

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-fb7dc96696914466a7ba71ba17802332
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08530593B2

Linked notes

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