Hydrochloric Acid → HCID 73197827, compound

HRID 1979133Notes

Reaction equation

HRID 1979133 reaction equation
[Cl: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.CO.O>[Cl: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

8

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 14116665HCID 14116665, compound

Product 1

HCID 73197827HCID 73197827, compoundYield 71.1%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

A mixture of 4-(4′-chloro-biphenyl-4-yl)-4-oxo-butyric acid (9.13 g, 0.0316 mol), hydroxylamine hydrochloride (2.64 g, 0.0380 mol), and sodium carbonate (4.04 g, 0.0381 mol) in absolute ethanol was refluxed under nitrogen for 13.5 hours and allowed to cool. The resulting suspension was filtered, and the filter cake was washed with ethanol followed by diethyl ether. The filter cake was dried under house vacuum to give a white solid. The solid was dissolved in methanol (450 mL), and the cloudy solution was filtered to remove fines. The filtrate was stirred while one equivalent of 1 M HCl was added dropwise followed by dropwise addition of deionized water (200 mL). The mixture was gently rotary evaporated (bath temperature=40° C.) to a volume of 150 mL. The solids that precipitated were chilled at 5° C. for 10 minutes and filtered. The filter cake was washed with water and dried in vacuo to give 6.82 g of 4-(4′-chloro-biphenyl-4-yl)-4-hydroxyimino-butyric acid as an off-white solid; mp 155-157° C.

Workup

  1. temperaturewas refluxed under nitrogen for 13.5 hours
  2. temperatureto cool
  3. filtrationThe resulting suspension was filtered
  4. washthe filter cake was washed with ethanol
  5. customThe filter cake was dried under house vacuum
  6. customto give a white solid
  7. filtrationthe cloudy solution was filtered
  8. customto remove fines
  9. additionwas added dropwise
  10. customThe mixture was gently rotary evaporated (bath temperature=40° C.) to a volume of 150 mL
  11. customThe solids that precipitated
  12. filtrationfiltered
  13. washThe filter cake was washed with water
  14. customdried in vacuo

Sources & evidence

ORD record
ord-3e051630bc9e4bc48e9c9d016c7fd2b0
Source dataset
uspto-grants-2001_05
Patent number
US06239288B1

Reaction notes

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