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

HRID 234809Notes

Reaction equation

HRID 234809 reaction equation
[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

Participants

6

Reactant 2

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

Product 2

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-938c4b627a594adeba7630e9fc7201e8
Source dataset
uspto-grants-1997_01
Patent number
US05596097

Reaction notes

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