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

HRID 2091543Notes

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. 1-1-(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-54eb93d1f5734296a6425e207c4085ed
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08440660B2

Reaction notes

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