Hydrochloric Acid → HCID 58978540, compound

HRID 1180340Notes

Reaction equation

HRID 1180340 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:15]=[CH:14][C:13]([O:16]C)=[CH:12][C:11]=2[CH3:18])[CH:5]=[CH:6][C:7]=1[CH:8]=[O:9].Cl.[NH+]1C=CC=CC=1.Cl>C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][C:11]=2[CH3:18])[CH:5]=[CH:6][C:7]=1[CH:8]=[O:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21584435Pyridinium hydrochlorideHCID 58978551HCID 58978551, compound

Product 1

HCID 58978540HCID 58978540, compoundYield 105.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3-Chloro-4′-methoxy-2′-methyl-1,1′-biphenyl-4-carbaldehyde (1.0 g, 3.84 mmol) and pyridinium HCl (6 g) in a sealed tube was heated at 195° C. with stirring for 1 hr. The reaction mixture was cooled to room temperature and stirred with 2 N HCl solution and ethyl acetate. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (×2). The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and evaporation of the solvent provided (1 g) dark green solid. The product was used without any further purification. An analytical sample was obtained by HPLC purification giving a white solid; mp 125-127° C.; 1H NMR (DMSO-d6): δ 2.21 (3H, s), 6.68-6.72 (2H, m), 7.11 (1H, d, J=8.15 Hz), 7.47 (1H, d, J=7.89 Hz), 7.55 (1H, d, J=1.48 Hz), 7.89 (1H, d, J=7.98 Hz), 9.62 (1H, s), 10.2=35 (1H, s); MS (ESI) m/z 245/247 (M−H)−, 247/249 (M+H)+.

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with ethyl acetate (×2)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporation of the solvent

Sources & evidence

ORD record
ord-4a70494356524cffb637705f7225c98e
Source dataset
uspto-grants-2007_10
Patent number
US07279600B2

Reaction notes

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