Water → HCID 10776253, compound

HRID 376738Notes

Reaction equation

HRID 376738 reaction equation
[C:1]1(=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[CH:3]=[CH:2]1.[CH3:13][N:14]1[CH:18]=[CH:17][CH:16]=[CH:15]1.O>C(O)(=O)C.ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:13][N:14]1[CH:18]=[CH:17][CH:16]=[C:15]1[C:3]1[C:4](=[O:11])[C:5]2[C:10]([C:1](=[O:12])[CH:2]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

7

Reactant 3

HCID 962WaterHCID 73041-MethylpyrroleHCID 85301,4-Naphthoquinone

Product 1

HCID 10776253HCID 10776253, compoundYield 79%

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

According to the procedure described in the article Chemistry Express 1990, Vol. 5, No. 10, pages 749-752, the disclosure of which is specifically incorporated by reference herein, 3.16 millimol of 1,4-naphthoquinone were stirred with 25 millimol of N-methylpyrrole and 3.16 millimol of copper acetate in 50 ml of acetic acid in a round-bottomed flask at room temperature for 1 hour. The reaction mixture was diluted with 300 ml of dichloromethane and the resulting mixture was then poured into a large volume of water (300 ml). The organic phase was then separated out and washed four times with 100 ml of water and finally with saturated aqueous NaCl solution. The resulting organic phase was dried over Na2SO4 and then concentrated under vacuum. The product 2-(1-methyl-1H-pyrrol-2-yl)-[1,4]-naphthoquinone was thus isolated in a yield of 79% after purification by chromatography on a column of silica.

Workup

  1. customThe organic phase was then separated out and
  2. washwashed four times with 100 ml of water
  3. dry with materialThe resulting organic phase was dried over Na2SO4
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-40c7303db7b6420d8d6428805b33ad5d
Source dataset
uspto-grants-2000_02
Patent number
US06022379

Reaction notes

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