Potassium Carbonate → 1-Methylanthracene

HRID 353317

Reaction equation

HRID 353317 reaction equation
OC[C:3]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10](CNC)=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[CH:8]2.[C:20]([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH3:20][C:11]1[C:16]2[C:15](=[CH:10][C:9]3[C:4]([CH:3]=2)=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 22353076(10-Methylaminomethyl-anthracen-9-yl)-methanol

Product 1

HCID 118841-MethylanthraceneYield 103.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

10-(hydroxymethyl)-9-((methylamino)methyl)anthracene (0.800 g, 3.18 mmol) and K2CO3 (0.56 g, 4.05 mmol) were taken up in 15 mL acetonitrile. A solution of 2,2-dimethylpropane-1,3-diyl(o-(bromomethyl)phenyl)boronate 3 (1.00 g, 3.44 mmol) in 5 mL acetonitrile was added and the mixture was refluxed under nitrogen for 24 h. The mixture was filtered hot on a sintered-glass frit and upon cooling, a yellow solid precipitated. The resulting solid was triturated with acetonitrile/water (4:1, v/v), filtered on a sintered-glass frit and vacuum dried to yield 11 as a bright yellow solid (0.632 g, 51.6% yield): 1H NMR (300.13 MHz, CD3OD) δ2.58 (s, 3H), 4.58 (s, 2H), 5.22 (s, 2H), 5.61 (s, 2H), 7.62 (m, 6H), 7.80 (m, 2H), 8.18 (m, 2H), 8.58 (m, 2H); 13C-{1H} NMR (75.4 MHz, CD3OD) δ136.9, 136.2, 135.9, 132.9, 132.7, 131.4, 129.9, 128.3, 127.1, 126.8, 126.5, 124.9, 124.1, 63.8, 57.1, 50.9, 40.7.

Workup

  1. temperaturethe mixture was refluxed under nitrogen for 24 h
  2. filtrationThe mixture was filtered hot on a sintered-glass frit
  3. temperatureupon cooling
  4. customa yellow solid precipitated
  5. customThe resulting solid was triturated with acetonitrile/water (4:1
  6. filtrationv/v), filtered on a sintered-glass frit and vacuum
  7. customdried

Sources & evidence

ORD record
ord-7d39d19b41bc4be28da0de1aa0b4cebb
Source dataset
uspto-grants-2004_06
Patent number
US06750311B1

Linked notes

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