Citric Acid → HCID 178515653, compound

HRID 384104Notes

Reaction equation

HRID 384104 reaction equation
[O:1]([C:8]1[N:13]=[C:12]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([CH:22]=[CH:23][C:24]([O:26]CC)=O)=[CH:18][CH:17]=2)[CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.[NH2:42][OH:43]>C(O)C.[OH-].[Na+]>[O:1]([C:8]1[N:13]=[C:12]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[O:43][N:42]=[C:24]([OH:26])[CH:23]=3)=[CH:18][CH:17]=2)[CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 311Citric AcidHCID 787HydroxylamineHCID 68431100Ethyl 3-(4-((6-phenoxypyridin-2-yl)methoxy)phenyl)prop-2-enoate

Product 1

HCID 178515653HCID 178515653, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of ethyl 3-(4-((6-phenoxypyridin-2-yl)methoxy)phenyl)prop-2-enoate (20.2 mg) in ethanol (1 ml), 0.05 ml of 50% aqueous hydroxylamine solution and 0.03 ml of 2N aqueous sodium hydroxide were added, and the reaction solution was stirred overnight at room temperature. The reaction solution was acidified with 10% aqueous citric acid, then extracted with chloroform, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and residue obtained was purified by preparative thin layer chromatography (Kieselgel™ 60 F254, Art5744, made by Merck & Co., chloroform/methanol (8:1)) to afford the title compound as a white solid.

Workup

  1. extractionextracted with chloroform
  2. dry with materialdried over anhydrous magnesium sulfate
  3. distillationThe solvent was distilled off under reduced pressure, and residue
  4. customobtained
  5. customwas purified by preparative thin layer chromatography (Kieselgel™ 60 F254, Art5744, made by Merck & Co., chloroform/methanol (8:1))

Sources & evidence

ORD record
ord-962afc41b1314bf083d1e294a959a087
Source dataset
uspto-grants-2013_02
Patent number
US08367708B2

Reaction notes

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