4-Hydroxybenzaldehyde → HCID 86651749, compound

HRID 1515093Notes

Reaction equation

HRID 1515093 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.F[C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([C:21]#[N:22])=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CC(C)C(N)=O>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([O:1][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]([C:21]#[N:22])=[CH:13][CH:12]=2)=[CH:3][CH:4]=1)=[O:7]

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 962WaterHCID 10796Cesium carbonateHCID 27367341-Cyano-4-fluoronaphthalene

Product 1

HCID 86651749HCID 86651749, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 68424IsobutyramideSolvent

Conditions

Temperature
120 °C

Procedure

4-Hydroxybenzaldehyde (300 mg, 2.46 mmol) was dissolved in dimethylacetoamide (8.0 mL), and 4-fluoro-naphthalene-1-carbonitrile (463 mg, 0.420 mmol) and cesium carbonate (1.20 g, 3.69 mmol) were sequentially added thereto at room temperature, and then, the resulting mixture was stirred under a nitrogen atmosphere at 120° C. for 2 hours. After the temperature of the reaction solution was returned to room temperature, water was added thereto, and the organic matter was extracted with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride solution, then dried over anhydrous sodium sulfate and filtered. Then, the solvent was distilled off under reduced pressure, whereby a crude product was obtained. This crude product was purified by silica gel column chromatography (hexane:ethyl acetate=95:5 to 70:30 (v/v)), whereby the objective title compound was obtained (515 mg, yield: 77%).

Workup

  1. customwas returned to room temperature
  2. extractionthe organic matter was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materiala saturated sodium chloride solution, then dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. distillationThen, the solvent was distilled off under reduced pressure, whereby a crude product
  7. customwas obtained
  8. customThis crude product was purified by silica gel column chromatography (hexane:ethyl acetate=95:5 to 70:30 (v/v)), whereby the objective title compound
  9. customwas obtained (515 mg, yield: 77%)

Sources & evidence

ORD record
ord-76c6388ba37044d99712c84b39ddbc7b
Source dataset
uspto-grants-2012_07
Patent number
US08222281B2

Reaction notes

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