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

HRID 456838Notes

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[N:14]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[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>>[C:24]1([N:14]2[C:15]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[CH:16][CH:17]=[C:13]2[C:8]2[CH:9]=[C:10]3[C:5](=[CH:6][CH:7]=2)[CH:4]=[C:3]([OH:2])[CH:12]=[CH:11]3)[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

Reactant 2

HCID 10176127Pyridinium chloride

HCID 184390222-(6-methoxy-2-naphthyl)-1,5-diphenyl-1H-pyrrole

Product 1

HCID 184390266-(1,5-diphenyl-1H-pyrrol-2-yl)-2-naphtholYield 83.1%

Conditions

Temperature: 205 °C

Procedure

In a similar manner as described in step 5 of Example 1, the title compound was prepared from 2-(6-methoxy-2-naphthyl)-1,5-dipheny-1H-pyrrol (1.25 g, 3.33 mmol), prepared in the previous step, and pyridine hydrochloride (30 g) with the exception that this reaction required heating at 205° C. Purification on silica gel (500 g, 200–300 mesh) using methylene chloride as the eluent gave 6-(1,5-diphenyl-1H-pyrrol-2-yl)-2-naphthol as a reddish solid (1.00 g, 83%), mp 222–223° C. Elemental Analysis for C26H19NO.0.11 C4H8O2 Calc'd: C, 85.57; H, 5.40; N, 3.77. Found: C, 85.28; H, 5.53; N, 3.73.

Workup

customPurification on silica gel (500 g, 200–300 mesh)

Sources & evidence

ORD record: ord-e8567c92687a4ea39dc0e62732bf77a7
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07186749B2

Reaction notes

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