Pyridinium chloride → HCID 135415976, compound

HRID 491704Notes

Reaction equation

HRID 491704 reaction equation
CO[C:3]1[CH:8]=[CH:7][C:6]([O:9]C)=[CH:5][C:4]=1[NH:11][C:12](=[O:23])[C:13]1[CH:18]=[C:17]([O:19]C)[CH:16]=[CH:15][C:14]=1[O:21]C.Cl.N1C=CC=CC=1>Cl>[OH:9][C:6]1[CH:7]=[CH:8][C:3]2[O:23][C:12]([C:13]3[CH:18]=[C:17]([OH:19])[CH:16]=[CH:15][C:14]=3[OH:21])=[N:11][C:4]=2[CH:5]=1

Participants

4

Reactant 2

HCID 10176127Pyridinium chlorideHCID 11370527HCID 11370527, compound

Product 1

HCID 135415976HCID 135415976, compoundYield 106.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of N-(2,5-dimethoxyphenyl)-2,5-dimethoxybenzamide (1.0 g, 3.1 mmol) and pyridine hydrochloride (2.0 g, 17.3 mmol) was stirred at 200° C. for 1 h. The mixture was cooled to room temperature and HCl (10 mL, 2 N) was added. The mixture was then extracted with EtOAc and the organic extracts were dried over MgSO4. Evaporation and purification by flash chromatography (hexanes/EtOAc 2/1) gave a white solid (0.8 g, 76% yield, m.p. 309-311° C.); MS m/e 242 (M−H)+.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionThe mixture was then extracted with EtOAc
  3. dry with materialthe organic extracts were dried over MgSO4
  4. customEvaporation and purification by flash chromatography (hexanes/EtOAc 2/1)

Sources & evidence

ORD record
ord-32193e24409941f8ae3731b7e69cf643
Source dataset
uspto-grants-2009_05
Patent number
US07531564B2

Reaction notes

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