Hydrochloric Acid → 2-Methyl-6-phenylpyridine

HRID 1084424

Reaction equation

HRID 1084424 reaction equation
[NH2:1]O.Cl.[C:4]([CH2:12][CH2:13][CH2:14][C:15](=O)[CH3:16])(=O)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>C(O)(=O)C>[CH3:16][C:15]1[CH:14]=[CH:13][CH:12]=[C:4]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:1]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 787HydroxylamineHCID 2385131-Phenyl-1,5-hexanedione

Product 1

HCID 27628852-Methyl-6-phenylpyridine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a refluxing mixture of hydroxylamine.HCl (2.1 g) in acetic acid (5 cc) was added a solution of 5-benzoyl-2-pentanone (1.9 g) (step 1) in acetic acid (5 cc) and the suspension refluxed for 3 hours. Acetic acid was then removed in vacuo, the residue treated with H2O (25 cc) and extracted with ethyl acetate (3×25 cc); the organic layer was washed with 25% aqueous NH4OAc, dilute NaHCO3 and brine. After removal of the solvent the residue was purified by chromatography to afford the title compound. p.m.r. (CD3CDCD3) δ 7.1-8.2 (m, 8H), 2.55 (s, 3H).

Workup

  1. temperaturethe suspension refluxed for 3 hours
  2. customAcetic acid was then removed in vacuo
  3. additionthe residue treated with H2O (25 cc)
  4. extractionextracted with ethyl acetate (3×25 cc)
  5. washthe organic layer was washed with 25% aqueous NH4OAc, dilute NaHCO3 and brine
  6. customAfter removal of the solvent the residue
  7. customwas purified by chromatography

Sources & evidence

ORD record
ord-ecf36a0096d144bd944f53d7401a9ee1
Source dataset
uspto-grants-1991_04
Patent number
US05004743

Linked notes

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