Ammonium Hydroxide → HCID 86749408, compound

HRID 2293827Notes

Reaction equation

HRID 2293827 reaction equation
[C:1]([CH:4]([CH:10]([C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1)[CH2:11][C:12](=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])(=O)[CH3:2].Cl.[NH2:28]O.[NH4+].[OH-]>CC(O)=O.O>[F:26][C:23]1[CH:24]=[CH:25][C:20]([C:10]2[CH:11]=[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:28]=[C:1]([CH3:2])[C:4]=2[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:21][CH:22]=1

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 86749407HCID 86749407, compound

Product 1

HCID 86749408HCID 86749408, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A mixture of α-acetyl-β-(4-fluorophenyl)-δ-oxobenzenepentanoic acid, ethyl ester (6.12 gm) and hydroxylamine hydrochloride (3.61 gm, 52 mmol) in glacial HOAc (83 ml) was refluxed for 1 hour. The reaction was cooled to room temperature and poured into an ice cold solution of concentrated NH4OH (115 ml) in H2O (300 ml). The resulting mixture was extracted twice with Et2O and the combined Et2O layers were washed with brine, dried (Na2SO4), filtered and stripped to yield a dark gummy residue. The residue was chromatographed (Flash, Merck SiO2, 8% EtOAc in hexane) to give 4-(4-fluorophenyl)-2-methyl-6-phenyl-3-pyridinecarboxylic acid, ethyl ester which was rechromatographed (8% EtOAc in hexane) to afford pyridine 4-(4-fluorophenyl)-2-methyl-6-phenyl-3-pyridinecarboxylic acid, ethyl ester (1.652 gm, 24% from (E)-3-(4-fluorophenyl)-1-phenyl-2-propen1-one) in >90% purity.

Workup

  1. temperaturewas refluxed for 1 hour
  2. extractionThe resulting mixture was extracted twice with Et2O
  3. washthe combined Et2O layers were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customto yield a dark gummy residue
  7. customThe residue was chromatographed (Flash, Merck SiO2, 8% EtOAc in hexane)

Sources & evidence

ORD record
ord-9abc4ef108b14ccf884cb701e39aa308
Source dataset
uspto-grants-1997_11
Patent number
US05686433

Reaction notes

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