1-Phenyl-1,2-propanedione → 2-methyl-3-phenylnaphthoquinone

HRID 1029347Notes

Reaction equation

HRID 1029347 reaction equation
N[C:2]1C(=O)C2[C:9]([C:10](=[O:13])[C:11]=1N)=[CH:8][CH:7]=[CH:6][CH:5]=2.[C:15]1([C:21](=O)[C:22](=[O:24])[CH3:23])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(O)(=O)C.O>[CH3:2][C:11]1[C:10](=[O:13])[C:9]2[C:23]([C:22](=[O:24])[C:21]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:5][CH:6]=[CH:7][CH:8]=2

Participants

4

Reactant 2

HCID 113631-Phenyl-1,2-propanedioneHCID 41672682,3-diaminonaphthalene-1,4-dione

Product 1

HCID 100148942-methyl-3-phenylnaphthoquinoneYield 94.5%

Reagents, catalysts & solvents 1

HCID 21899381Acetic acid--water (1/1)Solvent2×

Procedure

In a 200 ml Erlenmeyer flask were placed 5.0 g (26.5 mmols) of 2,3-diaminonaphthoquinone and 75 ml of acetic acid/water (1/1), then a solution composed of 5.9 g (39.8 mmols) of 1-phenyl-1,2-propanedione and 25 ml of acetic acid/water (1/1) was added dropwise to the mixture under ice-cooling over a period of about 10 minutes, and after stirring the mixture for 5 minutes, yellow precipitates formed were collected by filtration and washed with water. The precipitates were dissolved in methylene chloride; and, after purifying the solution by silica gel short column (eluted by methylene chloride), the product obtained was recrystallized from methylene chloride-methanol to provide 6.22 g (yield 78%) of 2-methyl-3-phenylnaphthoquinone as a yellow powder. Melting point 235°-236° C.

Workup

  1. additionwas added dropwise to the mixture under ice-
  2. temperaturecooling over a period of about 10 minutes
  3. customyellow precipitates
  4. customformed
  5. filtrationwere collected by filtration
  6. washwashed with water
  7. dissolutionThe precipitates were dissolved in methylene chloride
  8. customand, after purifying the solution
  9. washby silica gel short column (eluted by methylene chloride)
  10. customthe product obtained
  11. customwas recrystallized from methylene chloride-methanol

Sources & evidence

ORD record
ord-e5430a4f9956433fa84b5ba81c5f1e79
Source dataset
uspto-grants-1992_04
Patent number
US05102757

Reaction notes

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