Methyl iodide → 5-Hydroxymethyl-6-(2-methoxy-4-methoxymethoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline

HRID 1678335Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][O:10][CH3:11])[CH:5]=[CH:4][C:3]=1[C:12]1[C:13]([CH2:25][OH:26])=[C:14]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17]([CH3:23])([CH3:22])[CH:16]=[C:15]2[CH3:24].CI.[C:29](=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C.C(OCC)C>[OH:26][CH2:25][C:13]1[C:12]([C:3]2[CH:4]=[CH:5][C:6]([O:8][CH2:9][O:10][CH3:11])=[CH:7][C:2]=2[O:1][CH3:29])=[CH:21][CH:20]=[C:19]2[C:14]=1[C:15]([CH3:24])=[CH:16][C:17]([CH3:23])([CH3:22])[NH:18]2

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 6-(2-hydroxy-4-methoxymethoxyphenyl)-5-hydroxymethyl-2,2,4-trimethyl-1,2-dihydroquinoline (Reference Compound No. 1-(6), 746.1 mg, 2.10 mmol), methyl iodide (131 μL, 2.10 mmol) and potassium carbonate (582 mg, 4.21 mmol) was suspended in anhydrous N,N-dimethylformamide (10 mL) and the suspension was stirred at 50° C. for 1 hour. After cooling down, the mixture was diluted with ethyl acetate (50 mL) and diethylether (50 mL). The mixture was washed with water (100 mL, twice) and saturated brine (50 mL) successively, dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled reference compound (513.2 mg) as a colorless solid. (Yield 66%)

Workup

temperatureAfter cooling down
washThe mixture was washed with water (100 mL
dry with materialtwice) and saturated brine (50 mL) successively, dried over anhydrous magnesium sulfate
customthe solvent was removed under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record: ord-9564b8b3a11b41d280673e3a9e5e1cee
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08008498B2

Reaction notes

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