Pyridinium chloride → HCID 135415976, compound

HRID 1007316Notes

Reaction equation

HRID 1007316 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-de02ecaec9cb4cd4af14cca63fbb1e53
Source dataset
uspto-grants-2004_09
Patent number
US06794403B2

Reaction notes

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