Pyridinium chloride → HCID 10308089, compound

HRID 1071221Notes

Reaction equation

HRID 1071221 reaction equation
Cl.N1C=CC=CC=1.C[O:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[C:15](=[O:19])[CH:14]([C:20]1[CH:25]=[CH:24][C:23]([O:26]C)=[CH:22][CH:21]=1)[C:13]2=[O:28]>O>[OH:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[C:15](=[O:19])[CH:14]([C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1)[C:13]2=[O:28]

Participants

4

Reactant 2

HCID 10176127Pyridinium chlorideHCID 15882768HCID 15882768, compound

Product 1

HCID 10308089HCID 10308089, compoundYield 60.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Pyridine hydrochloride (400 mg) was heated to 190° C. To the melt was added 5-methoxy-2-(4-methoxyphenyl)-1H-inden-1,3(2H)-dione (150 mg, 0.53 mmol) and the reaction was stirred for 3 h. The mixture was cooled to room temperature and dissolved in water and extracted with ethyl acetate. The organic layers were combined and washed with 1 N HCl, water then brine and dried over MgSO4. Evaporation and flash chromatography (50%-60% EtOAc/petroleum ether) gave the product as a light brown solid, (81 mg, 60% yield, m.p. 227-228° C.); MS m/e 255 (M+H)+.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with 1 N HCl, water
  3. dry with materialbrine and dried over MgSO4
  4. customEvaporation and flash chromatography (50%-60% EtOAc/petroleum ether)

Sources & evidence

ORD record
ord-04f48710c28a409bbcac98153face6a8
Source dataset
uspto-grants-2005_06
Patent number
US06903238B2

Reaction notes

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