2-Chloroanthraquinone → 2-Methoxyanthraquinone

HRID 931873

반응식

HRID 931873 반응식
Cl[C:2]1[CH:15]=[CH:14][C:13]2[C:12](=[O:16])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[O:17])[C:4]=2[CH:3]=1.[CH3:18][O-:19].[Na+]>CN(C)C=O.CO>[CH3:18][O:19][C:2]1[CH:15]=[CH:14][C:13]2[C:12](=[O:16])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[O:17])[C:4]=2[CH:3]=1

참가 물질

5

반응물 2

HCID 85532-ChloroanthraquinoneHCID 10942334Sodium Methoxide

생성물 1

HCID 186462-Methoxyanthraquinone

시약·촉매·용매 2

HCID 887Methanol용매HCID 6228Dimethylformamide용매

반응 조건

온도
120 °C

실험 절차

First, the intermediate 2-methoxy-9,10-anthraquinone was prepared. A solution of 2-chloro-9,10-anthraquinone (10.08 g, 42 mmol) in 100 mL of N,N-dimethylformamide was treated with 25 mL of 25% sodium methoxide in methanol. The stirred reaction mixture was heated in a 120° C. oil bath for 6 h under nitrogen, then cooled to ambient. The product was precipitated into aqueous HCl (0.5 M, 250 mL), collected, washed with water and dried. The product was purified by recrystallization from a mixture of toluene and heptane to provide 1.6 g (16%) of a light yellow solid. This intermediate was characterized by 1H NMR: (300 MHz, CDCl3) δ 4.00 (s, 3H), 7.28 (d, 1H), 7.29 (d, 1H), 7.70 (m, 2H), 8.26 (s, 1H), 8.30 (m, 2H).

후처리

  1. customThe stirred reaction mixture
  2. temperaturecooled
  3. customThe product was precipitated into aqueous HCl (0.5 M, 250 mL)
  4. customcollected
  5. washwashed with water
  6. customdried
  7. customThe product was purified by recrystallization from a mixture of toluene and heptane

출처 및 근거

ORD 기록
ord-601ab51f2a804464a2c4b8ecaac37685
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09298088B2

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