Methylparaben → Methyl 4-(2-quinolinylmethoxy)benzoate

HRID 33819

Reaction equation

Cl[CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.[CH3:13][O:14][C:15](=[O:23])[C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+]>CC(C)=O.C(OCC)(=O)C>[CH3:13][O:14][C:15](=[O:23])[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:2][C:3]2[CH:12]=[CH:11][C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[N:4]=2)=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 2-Chloromethyl quinoline. (2 g, 9.3 mmole) in acetone (47 ml, 0.2M) was added 4-hydroxy benzoic acid methyl ester (1.42 g, 1.0 eq.) and potassium carbonate (3.86 g, 3 eq.). The reaction mixture was heated at 60° C. for 16 h under N2 atmosphere, cooled to ambient temperature and poured into 1N sodium hydroxide (50 ml)/ethyl acetate (100 ml). The layers were separated and the organic layer dried magnesium sulfate, filtered and concentrated. Biotage MPLC was run using a 5-30% ethyl acetate/hexane gradient on a 40 M column to provide the title compound as a white solid (1.66 g, 61%). 1H NMR (400 MHz, CDCl3) δ 8.18 (d, J=8.7 Hz, 1 H), 8.07 (d, J=8.3 Hz, 1 H), 7.95 (M, 2H), 7.82 (d, J=7.9 Hz, 1 H), 7.74 (dt, J=7.1, 1.7 Hz, 1 H), 7.62 (d, J=8.3 Hz, 1 H), 7.55 (dt, J=7.9, 1.2 Hz, 1 H), 7.03 (d, J=9.1, 2 H), 5.41 (s, 2 H), 3.84 (s, 3 H); MS: (M+H m/z=294.2).

Workup

temperaturecooled to ambient temperature
customThe layers were separated
filtrationthe organic layer dried magnesium sulfate, filtered
concentrationconcentrated

Sources & evidence

ORD record: ord-e5acc2e67ae741b183990732fc6b70ff
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07429665B2

Linked notes

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