Hydrochloric Acid → HCID 178436444, compound

HRID 2116502Notes

Reaction equation

HRID 2116502 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[C:8](=[O:17])[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH3:16])=[CH:11][CH:10]=1.Cl.C([O-])([O-])=[O:20].[Na+].[Na+]>OO>[CH2:15]([C:12]1[CH:13]=[CH:14][C:9]([C:8]([C:3]2[CH:4]=[N:5][CH:6]=[CH:7][C:2]=2[OH:20])=[O:17])=[CH:10][CH:11]=1)[CH3:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 23103649HCID 23103649, compound

Product 1

HCID 178436444HCID 178436444, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 784Hydrogen PeroxideCatalyst

Procedure

Next, to a solution of (4-chloropyridin-3-yl)-(4-ethylphenyl)methanol (3.2 g, 0.0129 mol) in chloroform (45 mL), Dess-Martin periodine (6.5 g, 0.0154 mol) was added under ice cooling and the reaction mixture was stirred at room temperature for 5 hours. After filtration to remove the precipitated insoluble materials, the filtrate was washed with 1M NaOH (40 mL) and saturated aqueous sodium chloride, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by NH silica gel chromatography (ethyl acetate) to give 4-chloro-3-(4-ethylbenzoyl)pyridine (3.4 g) as a yellow oil. A mixture of 4-chloro-3-(4-ethylbenzoyl)pyridine (3.4 g), 3M HCl (35 mL) and 30% H2O2 (2 drops) was heated under reflux for 6.5 hours. After cooling to room temperature, the reaction mixture was neutralized with Na2CO3. The resulting precipitate was filtered and washed with ethyl acetate to give 3-(4-ethylbenzoyl)-4-hydroxypyridine (2.9 g, 92% for 2 steps) as a light-yellow crystal.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 6.5 hours
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-eec5a066e1644c22a0b43caefd466d67
Source dataset
uspto-grants-2008_10
Patent number
US07439232B2

Reaction notes

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