Potassium Carbonate → HCID 73197828, compound

HRID 381818Notes

Reaction equation

HRID 381818 reaction equation
[Br: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.C(=O)([O-])[O-].[K+].[K+].Cl.[NH2:28][OH:29]>C(O)C.O.CO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14](=[N:28][OH:29])[CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 14116663HCID 14116663, compound

Product 1

HCID 73197828HCID 73197828, compoundYield 66.7%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a stirred suspension of 4-(4′-bromo-biphenyl-4-yl)-4-oxo-butyric acid (0.718 g, 0.00215 mol) and potassium carbonate (0.167 g, 0.00121 mol) in absolute ethanol (15 mL) was added a solution of hydroxylamine hydrochloride (0.180 g, 0.00259 mol) in water (3 mL), and the mixture stirred at room temperature for 6 days. The mixture was rotary evaporated. The residue was dissolved in methanol, silica gel (10 g) was added, and the mixture rotary evaporated to dryness. The powder was purified by chromatography on silica gel, eluting with dichloromethane-methanol (20:1) to give 0.499 g of 4-(4′-bromo-biphenyl-4-yl)-4-hydroxyimino-butyric acid as a white solid; mp 175-176° C.

Workup

  1. additionsilica gel (10 g) was added
  2. customthe mixture rotary evaporated to dryness
  3. customThe powder was purified by chromatography on silica gel
  4. washeluting with dichloromethane-methanol (20:1)

Sources & evidence

ORD record
ord-992441bb14d34c449edf70d0b3055d6b
Source dataset
uspto-grants-2001_10
Patent number
US06307089B2

Reaction notes

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