Toluene → HCID 86629168, compound

HRID 1095227Notes

Reaction equation

HRID 1095227 reaction equation
C[C:2]1[C:11]2[C:6](=[C:7]([C:13]#[C:14]CO)[CH:8]=[CH:9][C:10]=2[F:12])[N:5]=[C:4](C)[C:3]=1[CH3:18].[OH-].[Na+].C1(C)C=CC=CC=1>C(OCC)C>[F:12][C:10]1[CH:9]=[CH:8][C:7]([C:13]#[CH:14])=[C:6]2[C:11]=1[CH:2]=[C:3]([CH3:18])[CH:4]=[N:5]2

Participants

5

Reactant 3

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 66783832HCID 66783832, compound

Product 1

HCID 86629168HCID 86629168, compoundYield 50.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
120 °C

Procedure

Dimethylhydroxymethyl-5-fluoro-3-methyl-8-quinolylacetylene (336 mg, 1.38 mmol) and NaOH (55.2 mg, KISHIDA CHEMICAL CO., Ltd., 0.7 mm granular, 98 mass %, 1.38 mmol) were placed in a 300 mL two-neck flask equipped with a reflux condenser and the air inside the flask was replaced with Ar. 3.0 mL of toluene was added thereto and the mixture was refluxed at 120° C. for 30 minutes. Diethyl ether was added to the reaction mixture and the mixture was washed with a saturated aqueous ammonium chloride solution and dried over magnesium sulfate, followed by distilling off of the solvent under reduced pressure by an evaporator. The crude reaction product was purified by column chromatography (Hexane/AcOEt=100/0→1/10) using silica gel to give 130 mg of the desired compound as a brownish brown solid (yield: 50.7%).

Workup

  1. customequipped with a reflux condenser
  2. washthe mixture was washed with a saturated aqueous ammonium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. distillationby distilling off of the solvent under reduced pressure by an evaporator
  5. customThe crude reaction product
  6. customwas purified by column chromatography (Hexane/AcOEt=100/0→1/10)

Sources & evidence

ORD record
ord-2ab63d12ed4e48b480761e9bbb76f697
Source dataset
uspto-grants-2012_03
Patent number
US08137821B2

Reaction notes

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