3,4-Dimethoxyphenol → HCID 19754896, compound

HRID 1588902Notes

Reaction equation

HRID 1588902 reaction equation
[CH:1]1([N:6]([CH:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[C:7](=[O:15])[C:8]2[CH:13]=[CH:12][C:11](Br)=[CH:10][CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:21][O:22][C:23]1[CH:24]=[C:25]([OH:31])[CH:26]=[CH:27][C:28]=1[O:29][CH3:30]>N1C(C)=CC(C)=CC=1C>[CH:1]1([N:6]([CH:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[C:7](=[O:15])[C:8]2[CH:13]=[CH:12][C:11]([O:31][C:25]3[CH:26]=[CH:27][C:28]([O:29][CH3:30])=[C:23]([O:22][CH3:21])[CH:24]=3)=[CH:10][CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 162513,4-DimethoxyphenolHCID 54340316HCID 54340316, compound

Product 1

HCID 19754896HCID 19754896, compound

Reagents, catalysts & solvents 1

HCID 79532,4,6-TrimethylpyridineSolvent

Procedure

The reaction and workup were carried out in the same manner as described in Example 1 using p-bromobenzoic acid N,N-dicyclopentyl amide (1.839 g, 5.47 mmol), 3,4-dimethoxy phenol (876 mg, 5.68 mmol) and cuprous oxide (413 mg, 2.89 mmol) in 2,4,6-collidine (15 ml). The crude product was chromatographed on silica gel using mixtures of ethyl acetate and hexane as eluents to give the title compound as a crystalline solid that could be recrystallized from ethyl acetate and hexane, m. pt. 179.95° C. (DSC).

Workup

  1. customThe reaction and workup
  2. customThe crude product was chromatographed on silica gel using mixtures of ethyl acetate and hexane as eluents

Sources & evidence

ORD record
ord-967950e1fa27433e9a00994cd84bfbbd
Source dataset
uspto-grants-1993_06
Patent number
US05223539

Reaction notes

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