Potassium Carbonate → HCID 58704556, compound

HRID 17759Notes

Reaction equation

HRID 17759 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4](OB(O)O)[CH:5]=[CH:6][CH:7]=1.Cl[C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([CH3:23])[CH:19]=2)[N:14]=1.C(=O)([O-])[O-].[K+].[K+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1.C1COCC1.O>[CH3:1][C:2]1[CH:3]=[C:4]([C:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[C:18]([CH3:23])[CH:19]=3)[N:14]=2)[CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 779742-Chloro-6-methylquinolineHCID 222378353-Methylphenylboric acid

Product 1

HCID 58704556HCID 58704556, compound

Reagents, catalysts & solvents 4

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

3-methyl-phenyl-boric acid (1.3 mmol), 2-chloro-6-methyl-quinoline (1 mmol), tetrakis(triphenyl phosphine) palladium(0) (0.05 mmol), and potassium carbonate (3 mmol) are dissolved in a two-neck round bottom flask containing THF (30 ml) and H2O (10 ml). The mixture is then stirred for 24 hours in a bath of 100 degrees Celsius (C). Subsequently, when reaction no longer occurs, the THF and toluene are discarded. The mixture is extracted by using dichloromethane and water, which is then treated with vacuum distillation. Then, after filtering the mixture with a silica gel column, a solvent is treated with vacuum distillation. Thereafter, by using dichloromethane and petroleum ether, the mixture is re-crystallized and filtered, thereby yielding solid 2-(3-methylphenyl)-6-methyl-quinoline.

Workup

  1. customSubsequently, when reaction
  2. extractionThe mixture is extracted
  3. additionis then treated with vacuum distillation
  4. filtrationThen, after filtering the mixture with a silica gel column
  5. additiona solvent is treated with vacuum distillation
  6. customthe mixture is re-crystallized
  7. filtrationfiltered

Sources & evidence

ORD record
ord-ec77232869994d2980a45ec9a09d6335
Source dataset
uspto-grants-2010_06
Patent number
US07740957B2

Reaction notes

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