Hydrochloric Acid → 4-(4'-Fluoro-biphenyl-4-yl)4-hydroxyimino-butyric acid

HRID 381821Notes

Reaction equation

HRID 381821 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14](=O)[CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.Cl.[NH2:22][OH:23].C(=O)([O-])[O-].[Na+].[Na+].Cl>C(O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14](=[N:22][OH:23])[CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 107308704-(4'-Fluoro-4-biphenylyl)-4-oxo-butyric acid

Product 1

HCID 731978294-(4'-Fluoro-biphenyl-4-yl)4-hydroxyimino-butyric acidYield 92.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred mixture of 4-(4′-fluoro-biphenyl-4-yl)-4-oxo-butyric acid (2.72 g, 0.0100 mol), hydroxylamine hydrochloride (0.848 g, 0.0122 mol) and sodium carbonate (1.304 g, 0.0123 mol) in absolute ethanol (60 mL) was refluxed for 22 hours and allowed to cool. The solids were filtered, washed with additional ethanol, and allowed to air dry overnight. The solids were dissolve din methanol-water, and the solution acidified with 1.0 M hydrochloric acid (10 mL, 0.010 mol HCl). The mixture was concentrated to approximately 30 mL on a rotary evaporator, and the resulting precipitate filtered and dried in vacuo to give 2.66 g of 4-(4′-fluoro-biphenyl-4-yl)-4-hydroxyimino-butyric acid as a pale yellow solid; mp 152-153° C.

Workup

  1. temperaturewas refluxed for 22 hours
  2. temperatureto cool
  3. filtrationThe solids were filtered
  4. washwashed with additional ethanol
  5. customto air dry overnight
  6. dissolutionThe solids were dissolve din methanol-water
  7. concentrationThe mixture was concentrated to approximately 30 mL on a rotary evaporator
  8. filtrationthe resulting precipitate filtered
  9. customdried in vacuo

Sources & evidence

ORD record
ord-2237b87b49a44d18b0ed8559f5ff3c31
Source dataset
uspto-grants-2001_10
Patent number
US06307089B2

Reaction notes

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