Toluene → HCID 86629166, compound

HRID 1095223Notes

Reaction equation

HRID 1095223 reaction equation
C[C:2]1[C:3](C)=[N:4][C:5]2[C:10]([CH:11]=1)=[C:9]([F:12])[CH:8]=[C:7]([CH2:13][CH2:14][CH3:15])[C:6]=2[C:16]#[C:17]CO.[OH-].[Na+].C1(C)C=CC=CC=1>C(OCC)C>[F:12][C:9]1[CH:8]=[C:7]([CH2:13][CH2:14][CH3:15])[C:6]([C:16]#[CH:17])=[C:5]2[C:10]=1[CH:11]=[CH:2][CH:3]=[N:4]2

Participants

5

Reactant 3

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 66785466HCID 66785466, compound

Product 1

HCID 86629166HCID 86629166, compoundYield 67.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
120 °C

Procedure

Dimethylhydroxymethyl-5-fluoro-7-propyl-8-quinolylacetylene (390 mg, 1.44 mmol) and NaOH (88.0 mg, KISHIDA CHEMICAL CO., Ltd., 0.7 mm granular, 98%) were placed in a 30 mL Schlenk tube equipped with a reflux condenser and the air inside the flask was replaced with Ar. 5.0 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. The solvent was distilled off 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 206 mg of 5-fluoro-7-propyl-8-quinolylethyne as a yellow solid (yield: 66.6%).

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. distillationThe solvent was distilled off 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-bc3d39e23abc491e837f1bdc072ebcc2
Source dataset
uspto-grants-2012_03
Patent number
US08137821B2

Reaction notes

Loading…