Sodium Carbonate → 4-(4'-Cyano-biphenyl-4-yl)-4-hydroxyimino-butyric acid

HRID 1979163Notes

Reaction equation

HRID 1979163 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15](=O)[CH2:16][CH2:17][C:18]([OH:20])=[O:19])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)#[N:2].Cl.[NH2:23][OH:24].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15](=[N:23][OH:24])[CH2:16][CH2:17][C:18]([OH:20])=[O:19])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 183641364-(4'-Cyano-biphenyl-4-yl)-4-oxo-butyric acid

Product 1

HCID 734323184-(4'-Cyano-biphenyl-4-yl)-4-hydroxyimino-butyric acidYield 49.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred suspension of 4-(4′-cyano-biphenyl-4-yl)-4-oxo-butyric acid (0.7908 g, 0.002831 mol), hydroxylamine hydrochloride (0.2038 g, 0.00293 mol), sodium carbonate (0.3158 g, 0.00298 mol) in absolute ethanol (17 mL) was refluxed under nitrogen for 12 hours and allowed to cool. The mixture was allowed to stand for 2.5 days for convenience. Volatiles were rotary evaporated, and the residue was partitioned between dichloromethane-tetrahydrofuran (50/50 v/v) and 0.05 M aqueous hydrochloric acid (60 mL). The aqueous layer was extracted with additional organics. The extracts were combined, dried (Na2SO4) and rotary evaporated. The residue was dissolved/suspended in dichloromethane and chromatographed on silica gel (165 g, 230-400 mesh), eluting with dichloromethane-methanol (25:1, 30×125 mL; 15:1, 5×125 mL) to give 0.413 g of 4-(4′-cyano-biphenyl-4-yl)-4-hydroxyimino-butyric acid as an off-white solid; mp 157-159° C.

Workup

  1. temperaturewas refluxed under nitrogen for 12 hours
  2. temperatureto cool
  3. customthe residue was partitioned between dichloromethane-tetrahydrofuran (50/50 v/v) and 0.05 M aqueous hydrochloric acid (60 mL)
  4. extractionThe aqueous layer was extracted with additional organics
  5. dry with materialdried (Na2SO4) and rotary evaporated
  6. customchromatographed on silica gel (165 g, 230-400 mesh)
  7. washeluting with dichloromethane-methanol (25:1, 30×125 mL; 15:1, 5×125 mL)

Sources & evidence

ORD record
ord-e7a00d86d16d4dc6afb524c38e6e2e7b
Source dataset
uspto-grants-2001_05
Patent number
US06239288B1

Reaction notes

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