Pyridinium chloride → HCID 135415976, compound

HRID 858209Notes

Reaction equation

HRID 858209 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-353ec50418634478ba2a47ebb492130e
Source dataset
uspto-grants-2006_12
Patent number
US07148247B2

Reaction notes

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