Water → HCID 20701400, compound

HRID 428143Notes

Reaction equation

HRID 428143 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]([OH:21])[CH2:9][NH:10][C:11](=[O:20])/[CH:12]=[CH:13]/[C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[CH:5]=[CH:6][CH:7]=1.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.O>CN(C)C=O>[OH:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[C:8](=[O:21])[CH2:9][NH:10][C:11](=[O:20])/[CH:12]=[CH:13]/[C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2724130Cornforth reagentHCID 20701425HCID 20701425, compound

Product 1

HCID 20701400HCID 20701400, compoundYield 30.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (E)-N-[2-(3-hydroxyphenyl)-2-hydroxyethyl]-3-(3-pyridyl)-2-propenoic acid amide (568 g, 2 mmol) in dimethylformamide (4 ml), pyridinium dichromate (1.28 g, 1.7 eq.) was added under ice-cooling and stirred at room temperature for 10 hours. Then, water (4 ml) was added. Tar materials were filtered out on Celite and water (4 ml) was added to the filtrate and extracted with ethyl acetate. The solvent was distilled out under reduced pressure and the residue was solidified in ethanol to yield the titled compound (171 mg, 30%).

Workup

  1. temperaturecooling
  2. filtrationTar materials were filtered out on Celite and water (4 ml)
  3. additionwas added to the filtrate
  4. extractionextracted with ethyl acetate
  5. distillationThe solvent was distilled out under reduced pressure

Sources & evidence

ORD record
ord-fa7843c6998449f99ff8739fb538a42c
Source dataset
uspto-grants-2001_11
Patent number
US06313153B1

Reaction notes

Loading…