Pyridinium chloride → HCID 22221618, compound

HRID 1794539Notes

Reaction equation

HRID 1794539 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

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% Et OActHex) to give 123 as a solid (0.25 g, 74%): Mp=274–276° C., 1H NMR (DMSO-6) δ 9.96 (br s, 1 H), 9.52 (br s, 1 H), 7.74 (d, 2 H, J=8.4 Hz), 7.17–7.16 (m, 3 H), 6.89 (d, 2 H, J=8.4 Hz),2.64 (s, 3 H); MS 267 (M−H)−

Workup

  1. temperature.was heated
  2. customto 200° C
  3. temperaturethe reaction was cooled
  4. extractionextracted with EtOAc
  5. dry with materialThe EtOAc layer was dried over MgSO4
  6. concentrationconcentrated
  7. customthe product was purified by column chromatography (50% Et OActHex)

Sources & evidence

ORD record
ord-673bdd127b434f19a1f032245a0ff56b
Source dataset
uspto-grants-2006_04
Patent number
US07022733B2

Reaction notes

Loading…