2-Methyl-8-aminoquinoline → 2-Methyl-N-[1-naphthyl(phenyl)methyl]quinolin-8-amine

HRID 41325

Reaction equation

[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([NH2:12])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.Br[CH:14]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1>C(N(CC)CC)C>[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([NH:12][CH:14]([C:15]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH:18]=[CH:17][CH:16]=3)[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 2.05 g (13.0 mmol) of 2-methyl-8-aminoquinoline, 2.53 g (25 mmol) of triethylamine and 7.43 g (25 mmol) of 8 was stirred for 2 hr at 120° C. One more portion of 2.53 g of triethylamine as well as 7.43 g of 8 was added. The resulting mixture was stirred for additional 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 0.56 g (12%) of the title compound A5.

Workup

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

Sources & evidence

ORD record: ord-5232dbda52684d7f9ddf2641db446d1f
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08530593B2

Linked notes

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