Pyridinium chloride → HCID 22221618, compound

HRID 1836043Notes

Reaction equation

HRID 1836043 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C:20](=[O:22])[CH3:21])[C:6]2[O:10][C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17]C)=[CH:13][CH:12]=3)=[CH:8][C:7]=2[CH:19]=1.Cl.N1C=CC=CC=1>O>[OH:2][C:3]1[CH:4]=[C:5]([C:20](=[O:22])[CH3:21])[C:6]2[O:10][C:9]([C:11]3[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=3)=[CH:8][C:7]=2[CH:19]=1

Participants

4

Reactant 2

HCID 10176127Pyridinium chlorideHCID 22221637HCID 22221637, compound

Product 1

HCID 22221618HCID 22221618, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of 122 (0.37 g, 1.3 mmol) and Pyridine HCl (10 g) was heated to 200° C. After 1 hr, the reaction was cooled, diluted with water and extracted with EtOAc. The EtOAc layer was dried over MgSO4, concentrated and the product was purified by column chromatography (50% EtOAc/Hex) to give 123 as a solid (0.25 g, 74%): Mp=274-276° C.;

Workup

  1. temperaturethe reaction was cooled
  2. extractionextracted with EtOAc
  3. dry with materialThe EtOAc layer was dried over MgSO4
  4. concentrationconcentrated
  5. customthe product was purified by column chromatography (50% EtOAc/Hex)

Sources & evidence

ORD record
ord-9c361842ec4b496398796f369029f40e
Source dataset
uspto-grants-2004_08
Patent number
US06774248B2

Reaction notes

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