Aluminum(III) Chloride → HCID 178479873, compound

HRID 1241697Notes

Reaction equation

HRID 1241697 reaction equation
C[O:2][C:3]1[C:16]2=NC3C(C=[C:15]2[C:14]2[CH:13]=[C:12]4[C:7]([CH:8]=[CH:9][CH:10]=[CH:11]4)=[N:6][C:5]=2[CH:4]=1)=CC=CC=3.[Cl-].[Al+3].[Cl-].[Cl-]>C1C=CC=CC=1>[OH:2][C:3]1[CH:16]=[C:15]2[C:14]3[C:13](=[C:12]4[C:7](=[N:6][C:5]=3[C:14]3[CH:15]=[CH:16][CH:3]=[CH:4][C:5]=3[N:6]2[CH3:7])[CH:8]=[CH:9][CH:10]=[CH:11]4)[CH:4]=1

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 86591638HCID 86591638, compound

Product 1

HCID 178479873HCID 178479873, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
80 °C

Procedure

(Method K) (Demethylation) The appropriate 6-methoxyquinoacridine was suspended in benzene and anhydrous aluminium chloride added (3 eq). The mixture was heated to 80° C., giving a red oily suspension and bright green haze on the solvent, until complete reaction was seen by tlc (0.2 mL sample, 0.5 mL methanol quench, 0.2 mL sat. aq. NaHCO3 neutralisation, neat EtOAC eluent) then allowed to cool to room temperature. Methanol was added slowly with ice cooling of the suspension and the stirring continued until all red oil was gone. The solvent was evaporated under reduced pressure, and the residue treated with sat. aq. sodium hydrogen carbonate. The organics were separated form the crude filtrate by soxhlet extraction with ethyl acetate. Filtration of the precipitate on cooling gave the desired compound.

Workup

  1. customgiving a red oily suspension and bright green haze on the solvent
  2. customuntil complete reaction
  3. customwas seen by tlc (0.2 mL sample, 0.5 mL methanol quench, 0.2 mL sat. aq. NaHCO3 neutralisation, neat EtOAC eluent)
  4. temperatureto cool to room temperature
  5. additionMethanol was added slowly with ice
  6. temperaturecooling of the suspension
  7. customThe solvent was evaporated under reduced pressure
  8. additionthe residue treated with sat. aq. sodium hydrogen carbonate
  9. customThe organics were separated form the crude filtrate
  10. extractionby soxhlet extraction with ethyl acetate
  11. filtrationFiltration of the precipitate
  12. temperatureon cooling

Sources & evidence

ORD record
ord-a30e72316515484e92f89c79bba4cf62
Source dataset
uspto-grants-2006_10
Patent number
US07115619B2

Reaction notes

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