N-Methyl-4-anisidine → (4-Methoxy-phenyl)-methyl-(quinolin-4-yl)-amine

HRID 1876102Notes

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][CH3:21])=[CH:16][CH:15]=1>>[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]([CH3:21])[C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=[CH:4][CH:3]=2)=[CH:16][CH:15]=1

Participants

Reactant 2

HCID 22250N-Methyl-4-anisidine

HCID 691404-Chloroquinoline

Product 1

HCID 11219278(4-Methoxy-phenyl)-methyl-(quinolin-4-yl)-amineYield 74.2%

Conditions

Temperature: 140 °C

Procedure

A mixture of 4-chloroquinoline (50 mg, 0.31 mmol) and (4-methoxy-phenyl)-methyl amine (300 mg, 2.2 mmol) was heated in a sealed tube at 140° C. overnight. The crude product was purified by chromatography (20-40% ethyl acetate/hexanes) on silica gel to give the title compound (60 mg, 0.23 mmol, 74%). 1H NMR (CDCl3): 8.77 (d, 1H, J=5.1), 8.00-8.04 (m, 1H), 7.61-7.64 (m, 1H), 7.55 (ddd, 1H, J=1.5, 6.9, 8.4), 7.22 (ddd, 1H, J=1.5, 6.9, 8.1), 6.99 (d, 1H, J=4.8), 6.92 (m, 2H), 6.89 (m, 2H), 3.77 (s, 3H), 3.43 (s, 3H).

Workup

customThe crude product was purified by chromatography (20-40% ethyl acetate/hexanes) on silica gel

Sources & evidence

ORD record: ord-5bd92757a8ac4129841eec6f3fd7f0fa
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08309562B2

Reaction notes

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