Toluene → HCID 86629169, compound

HRID 1095230Notes

Reaction equation

HRID 1095230 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]([CH2:17][CH2:18][CH3:19])[C:3]=1C.[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]=[CH:3][C:4]([CH2:17][CH2:18][CH3:19])=[N:5]2

Participants

5

Reactant 3

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 66784250HCID 66784250, compound

Product 1

HCID 86629169HCID 86629169, compoundYield 97.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
120 °C

Procedure

Dimethylhydroxymethyl-5-fluoro-2-propyl-8-quinolylacetylene (326 mg, 1.20 mmol) and NaOH (KISHIDA CHEMICAL CO., Ltd., 0.7 mm granular, 98 mass % article, 88.6 mg (2.22 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 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 250 mg of the desired compound as a yellow solid (yield: 97.5%).

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-0af69cf3d2614d56a2f8f219396ca59a
Source dataset
uspto-grants-2012_03
Patent number
US08137821B2

Reaction notes

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