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

HRID 1029348Notes

Reaction equation

HRID 1029348 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 of Erlenmeyer flask were placed 5.0 g (26.5 mmols) of 2,3-diaminonaphthoquinone and 75 ml of acetic acid/water (1/1), 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 thus formed were collected by filtration and washed with water. The precipitates were dissolved in methylene chloride, and after purifying the product with silica gel short column (eluted by methylene chloride), the product was recrystallized from methylene chloridemethanol to provide 6.22 g (78%) of 2-methyl-3-phenylnaphthoquinone (Compound Id-11) as a yellow powder. Melting point 235°-236° C. The infrared spectrum of the compound obtained is shown in FIG. 7.

Workup

  1. additionwas added dropwise to the mixture under ice-
  2. temperaturecooling over a period of about 10 minutes
  3. customyellow precipitates thus
  4. customformed
  5. filtrationwere collected by filtration
  6. washwashed with water
  7. dissolutionThe precipitates were dissolved in methylene chloride
  8. customafter purifying the product
  9. washwith silica gel short column (eluted by methylene chloride)
  10. customthe product was recrystallized from methylene chloridemethanol

Sources & evidence

ORD record
ord-312c0d490f8b46fa90f53878cd982a4d
Source dataset
uspto-grants-1992_04
Patent number
US05102757

Reaction notes

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