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

HRID 1043675
Notes
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Reaction equation

HRID 1043675 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 579906086-(2-Hydroxy-4-methoxymethoxyphenyl)-5-hydroxymethyl-2,2,4-trimethyl-1,2-dihydroquinoline

Product 1

HCID 579905855-Hydroxymethyl-6-(2-methoxy-4-methoxymethoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinolineYield 66%

Reagents, catalysts & solvents 3

HCID 3283
Diethyl Ether
Solvent
HCID 6228DimethylformamideSolvent
HCID 8857Ethyl AcetateSolvent

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

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

Sources & evidence

ORD record
ord-226c30692c684b858262fca433f0b71e
Source dataset
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08563551B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes