3,4-Dimethoxyphenol → HCID 19754871, compound

HRID 1588901Notes

Reaction equation

HRID 1588901 reaction equation
[CH:1]([N:4]([CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)[C:5](=[O:13])[C:6]1[CH:11]=[CH:10][C:9](Br)=[CH:8][CH:7]=1)([CH3:3])[CH3:2].[CH3:20][O:21][C:22]1[CH:23]=[C:24]([OH:30])[CH:25]=[CH:26][C:27]=1[O:28][CH3:29]>N1C(C)=CC(C)=CC=1C>[CH:14]1([N:4]([CH:1]([CH3:3])[CH3:2])[C:5](=[O:13])[C:6]2[CH:11]=[CH:10][C:9]([O:30][C:24]3[CH:25]=[CH:26][C:27]([O:28][CH3:29])=[C:22]([O:21][CH3:20])[CH:23]=3)=[CH:8][CH:7]=2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 162513,4-DimethoxyphenolHCID 19754886HCID 19754886, compound

Product 1

HCID 19754871HCID 19754871, 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-isopropyl-N-cyclohexyl amide (2.820 g, 8.70 mmol), 3,4-dimethoxy phenol (1.347 g, 8.74 mmol) and cuprous oxide (647 mg, 4.52 mmol) in 2,4,6-collidine (20 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. 106.85° 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-55acfa0f90144f55923811080f6e5e9e
Source dataset
uspto-grants-1993_06
Patent number
US05223539

Reaction notes

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