Methylamine → 2-(6-methoxy-2-naphthyl)-1-methyl-5-phenyl-1H-pyrrole

HRID 456824Notes

Reaction equation

HRID 456824 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.[CH3:25][NH2:26]>>[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:26]([CH3:25])[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 6329MethylamineHCID 184390201-(6-Methoxy-2-naphthyl)-4-phenylbutane-1,4-dione

Product 1

HCID 184390232-(6-methoxy-2-naphthyl)-1-methyl-5-phenyl-1H-pyrroleYield 85%

Procedure

In a similar manner as described in step 4 of Example 1, the title compound was prepared from 1-(6-methoxy-2-naphthyl)-4-phenylbutane-1,4-dione (3.00 g, 9.42 mmol), prepared in step 3 of Example 1, and methyl amine (8 M solution in EtOH, 100 mL, 800 mmol). Isolation of the solids by vacuum filtration gave 2-(6-methoxy-2-naphthyl)-1-methyl-5-phenyl-1H-pyrrole as a white solid (2.5 g, 85%), mp 197–198° C. Elemental Analysis for C22H19NO Calc'd: C, 84.31; H, 6.11; N, 4.47. Found: C, 84.47; H, 6.08; N, 4.41.

Workup

  1. filtrationIsolation of the solids by vacuum filtration

Sources & evidence

ORD record
ord-c62a138a99f1448aa3fa019f0768b37e
Source dataset
uspto-grants-2007_03
Patent number
US07186749B2

Reaction notes

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