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

HRID 1029348노트

반응식

HRID 1029348 반응식
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

참가 물질

4

반응물 2

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

생성물 1

HCID 100148942-methyl-3-phenylnaphthoquinone수율 94.5%

시약·촉매·용매 1

HCID 21899381Acetic acid--water (1/1)용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-312c0d490f8b46fa90f53878cd982a4d
출처 데이터셋
uspto-grants-1992_04
특허 번호
US05102757

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