Aluminum(III) Chloride → 9-Fluoro-6-hydroxybenzo[g]isoquinoline-5,10-dione

HRID 440354

반응식

HRID 440354 반응식
[Cl-:1].[Al+3].[Cl-].[Cl-].C[O:6][C:7]1[C:12]2[C:13](=[O:22])[C:14]3[CH:15]=[CH:16][N:17]=[CH:18][C:19]=3[C:20](=[O:21])[C:11]=2[C:10]([F:23])=[CH:9][CH:8]=1>C(Cl)Cl.O>[F:23][C:10]1[C:11]2[C:20](=[O:21])[C:19]3[CH:18]=[N:17][CH:16]=[CH:15][C:14]=3[C:13](=[O:22])[C:12]=2[C:7]([OH:6])=[CH:8][CH:9]=1.[Cl:1][C:10]1[C:11]2[C:20](=[O:21])[C:19]3[CH:18]=[N:17][CH:16]=[CH:15][C:14]=3[C:13](=[O:22])[C:12]=2[C:7]([OH:6])=[CH:8][CH:9]=1

참가 물질

6

반응물 2

HCID 6451240Aluminum(III) ChlorideHCID 104913596-Methoxy-9-fluorobenzo[g]isoquinoline-5,10-dione

생성물 2

HCID 105143529-Fluoro-6-hydroxybenzo[g]isoquinoline-5,10-dioneHCID 107777069-Chloro-6-hydroxybenzo[g]isoquinoline-5,10-dione

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매2회

실험 절차

Aluminum chloride (19.05 g) is added in one portion to a stirred refluxing solution of 6-methoxy-9-fluorobenzo[g]isoquinoline-5,10-dione (7.20 g) in methylene chloride (432 mL). After refluxing for 4 hours the reaction mixture is cooled and poured in water (1,300 mL). Methylene chloride (200 mL) is added and after stirring for 10 min the organic phase is separated. The aqueous solution is saturated with NaCl and further extracted with methylene chloride (3×400 mL). The combined organic solutions are washed with brine (1,000 mL), dried and the solvent removed by roto-evaporation. The brown solid obtained (6.5 g) is recrystallized from ethyl acetate/n-hexane 1/1 (65 mL) to yield a 9/1 mixture (1H-NMR evaluation) of 9-fluoro-6-hydroxybenzo[g] isoquinoline-5,10-dione and 9-chloro-6-hydroxybenzo[g] isoquinoline-5,10-dione respectively (6.00 g).

후처리

  1. temperatureAfter refluxing for 4 hours the reaction mixture
  2. temperatureis cooled
  3. customis separated
  4. extractionfurther extracted with methylene chloride (3×400 mL)
  5. washThe combined organic solutions are washed with brine (1,000 mL)
  6. customdried
  7. customthe solvent removed by roto-evaporation
  8. customThe brown solid obtained (6.5 g)
  9. customis recrystallized from ethyl acetate/n-hexane 1/1 (65 mL)

출처 및 근거

ORD 기록
ord-fe79c1ea2ab346b886f1323b703f5711
출처 데이터셋
uspto-grants-1996_05
특허 번호
US05519029

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