Pyridine → 4'-Hydroxy-3-methyl[1,1'-biphenyl]-4-carbaldehyde oxime

HRID 1180341Notes

Reaction equation

HRID 1180341 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH:14]=O)=[C:10]([CH3:16])[CH:9]=2)=[CH:4][CH:3]=1.Cl.[NH2:18][OH:19].N1C=CC=CC=1>CO>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH:14]=[N:18][OH:19])=[C:10]([CH3:16])[CH:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 589785354'-Hydroxy-3-methyl[1,1'-biphenyl]-4-carbaldehyde

Product 1

HCID 1363385954'-Hydroxy-3-methyl[1,1'-biphenyl]-4-carbaldehyde oximeYield 53.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4′-hydroxy-3-methyl[1,1′-biphenyl]-4-carbaldehyde (310 mg, 1.46 mmol), hydroxylamine hydrochloride (203 mg, 2.92 mmol) and pyridine (236 ul, 2.92 mmol) in 15 mL absolute methanol was refluxed for 2.5 h. The solvent was removed under reduced pressure and the mixture was dissolved in ethyl acetate and water, extracted with ethyl acetate (×3), washed with brine, dried over sodium sulfate, and filtered. Evaporation of the solvent and purification by recrystallization (ethyl acetate, acetone and hexane) gave 177 mg (53%) of the title compound as a yellowish solid: mp 195-197° C.;

Workup

  1. temperaturewas refluxed for 2.5 h
  2. customThe solvent was removed under reduced pressure
  3. dissolutionthe mixture was dissolved in ethyl acetate
  4. extractionwater, extracted with ethyl acetate (×3)
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customEvaporation of the solvent and purification
  9. customby recrystallization (ethyl acetate, acetone and hexane)

Sources & evidence

ORD record
ord-21fd4b15355241d69a6a548fdafd7108
Source dataset
uspto-grants-2007_10
Patent number
US07279600B2

Reaction notes

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