Pyridinium chloride → 6-(5-phenyl-1H-pyrrol-2-yl)-2-naphthol

HRID 456813Notes

Reaction equation

HRID 456813 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:13]1[NH:14][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:16][CH:17]=1)[CH:7]=[CH:6]2.Cl.N1C=CC=CC=1>Cl>[C:18]1([C:15]2[NH:14][C:13]([C:8]3[CH:9]=[C:10]4[C:5](=[CH:6][CH:7]=3)[CH:4]=[C:3]([OH:2])[CH:12]=[CH:11]4)=[CH:17][CH:16]=2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 10176127Pyridinium chlorideHCID 184390252-(6-methoxy-2-naphthyl)-5-phenyl-1H-pyrrole

Product 1

HCID 184390376-(5-phenyl-1H-pyrrol-2-yl)-2-naphtholYield 95%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of 2-(6-methoxy-2-naphthyl)-5-phenyl-1H-pyrrole (0.72 g, 2.4 mmol), prepared in the previous step, and pyridine hydrochloride (7.2 g) was heated at 200° C. under a nitrogen atmosphere for 1 hour. The mixture was cooled to ambient temperature and the solids were dissolved in 1N HCl (150 mL). The mixture was extracted three times with methylene chloride. The combined extracts were washed one time with water, dried (MgSO4), filtered and the solvent removed under reduced pressure to give 6-(5-phenyl-1H-pyrrol-2-yl)-2-naphthol as a grayish solid (0.65 g, 95%), mp 209.5–210.5 Elemental Analysis for C20H15NO Calc'd: C, 84.19; H, 5.30; N, 4.91. Found: C, 83.38; H, 5.38; N, 4.67.

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. extractionThe mixture was extracted three times with methylene chloride
  3. washThe combined extracts were washed one time with water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-6f1aba1d10a04adb851ff0805e891b20
Source dataset
uspto-grants-2007_03
Patent number
US07186749B2

Reaction notes

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