Pyridinium chloride → HCID 44254688, compound

HRID 2220590Notes

Reaction equation

HRID 2220590 reaction equation
Cl.N1C=CC=CC=1.C[O:9][C:10]1[CH:11]=[C:12]([C:16]2[O:17][C:18]3[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[CH:21][C:19]=3[CH:20]=2)[CH:13]=[CH:14][CH:15]=1>O.Cl>[OH:9][C:10]1[CH:11]=[C:12]([C:16]2[O:17][C:18]3[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[CH:21][C:19]=3[CH:20]=2)[CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 10176127Pyridinium chlorideHCID 44254158HCID 44254158, compound

Product 1

HCID 44254688HCID 44254688, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

To a melted pyridine hydrochloride (15.0 g) at 160-180° C. was added 2-(3-methoxyphenyl)benzofuran-5-carbonitrile (120) in one portion and the stirring continued at 180° C. for 2.5 h. The mixture was cooled down, diluted with water (100 mL) and 1 M HCl (50 mL) and stirred at room temperature for 30 min. A precipitate formed was separated, washed with 1 M HCl (150 mL) and water (150 mL) and dried. The residue was purified by flash chromatography (silica gel, EtOAc/hexanes 1/3) followed by recrystallization to give 125 as white solid (1.50 g, 69%): mp 222-224° C. (EtOAc/hexanes). 1H NMR (DMSO-d6) δ9.78 (d, J=1.1 Hz, 1H), 8.21 (br s, 1H), 7.85 (d, J=8.2 Hz, 1H), 7.75 (ddd, J=8.2, 1.6, 1.1 Hz, 1H), 7.48 (s, 1H), 7.40 (dd, J=8.2, 1.1 Hz, 1H), 7.33 (dd, J=8.2, 7.7 Hz, 1H), 6.86 (ddd, J=8.2, 2.2, 1.1 Hz, 1H). HPLC (method B) tR 5.70 min (100.0 area %). Anal. (C15H9NO2) C, H, N.

Workup

  1. temperatureThe mixture was cooled down
  2. customA precipitate formed
  3. customwas separated
  4. washwashed with 1 M HCl (150 mL) and water (150 mL)
  5. customdried
  6. customThe residue was purified by flash chromatography (silica gel, EtOAc/hexanes 1/3)
  7. customfollowed by recrystallization

Sources & evidence

ORD record
ord-adb511495aef430f8011dc0fd4525b9b
Source dataset
uspto-grants-2008_08
Patent number
US07417158B2

Reaction notes

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