Aniline → 2-(6-methoxy-2-naphthyl)-1,5-diphenyl-1H-pyrrole

HRID 456837Notes

Reaction equation

HRID 456837 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:13](=O)[CH2:14][CH2:15][C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=O)[CH:7]=[CH:6]2.[NH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>>[CH3:1][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:25]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:15][CH:14]=1)[CH:7]=[CH:6]2

Participants

3

Reactant 2

HCID 6115AnilineHCID 184390201-(6-Methoxy-2-naphthyl)-4-phenylbutane-1,4-dione

Product 1

HCID 184390222-(6-methoxy-2-naphthyl)-1,5-diphenyl-1H-pyrroleYield 77%

Procedure

In a similar manner as described in step 1 of Example 8, the title compound was prepared from 1-(6-methoxy-2-naphthyl)-4-phenylbutane-1,4-dione (1.50 g, 4.71 mmol), prepared in step 3 of Example 1, and aniline (3.07 g, 33.0 mmol). Purification on silica gel (500 g, 200–300 mesh) using 0% to 50% methylene chloride in hexane as the eluent gave 2-(6-methoxy-2-naphthyl)-1,5-diphenyl-1H-pyrrole as an off-white solid (1.36 g, 77%), mp 199–200° C. Elemental Analysis for C27H21NO.0.11 CH2Cl2 Calc'd: C, 84.62; H, 5.56; N, 3.64. Found: C, 84.55; H, 5.67; N, 3.61.

Workup

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

Sources & evidence

ORD record
ord-310722294d214067b5084fd252efff51
Source dataset
uspto-grants-2007_03
Patent number
US07186749B2

Reaction notes

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