Phenol → 9-Phenoxyacridine

HRID 2209311Notes

Reaction equation

HRID 2209311 reaction equation
[CH:1]1[C:14]2[C:13](=[O:15])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.O=S(Cl)Cl.[C:20]1(O)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C1C=CC=CC=1>[O:15]([C:13]1[C:12]2[C:7]([N:6]=[C:5]3[C:14]=1[CH:1]=[CH:2][CH:3]=[CH:4]3)=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 996PhenolHCID 2015AcridoneHCID 11430Potassium CarbonateHCID 24386Thionyl Chloride

Product 1

HCID 1006409-PhenoxyacridineYield 98%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Dry benzene (450 mL) was added to 1.50 g acridone (1 equiv.) under N2-atmosphere. SOCl2 (3.37 mL, 6 equiv.) was added and the reaction mixture was refluxed over night followed by removal of solvent by evaporation. Dry DMF (75 mL), phenol (2.17 g, 3 equiv.) and K2CO3 (4.26 g, 3 equiv.) were added under N2. The reaction was stirred at 60° C. for 3.5 days. After filtration and evaporation the crude product was purified using flash chromatography (CH2Cl2 to CH2Cl2:Et2O, 6:1) giving 2.04 g of 2, 98% yield. 1H NMR (CDCl3): 8.28 (5+4, br ddd, J=8.9, 1.1, 0.8 Hz, 2H), 8.11 (8+1, ddd, J=8.7, 1.3, 0.8 Hz, 2H), 7.79 (6+3, ddd, J=8.9, 6.6, 1.3 Hz, 2H), 7.47 (7+2, ddd, J=8.7, 6.6, 1.1 Hz, 2H), 7.28 (2′+4′, m, 2H), 7.06 (3′, m, 1H), 6.86 (1′+5′, m, 2H). 3.40 (6, m, 2H).

Workup

  1. temperaturethe reaction mixture was refluxed over night
  2. customfollowed by removal of solvent by evaporation
  3. filtrationAfter filtration and evaporation the crude product
  4. customwas purified

Sources & evidence

ORD record
ord-dd21f684319d4d219b6a290b8fcf1573
Source dataset
uspto-grants-2016_06
Patent number
US09377466B2

Reaction notes

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