Pyridine → HCID 18006778, compound

HRID 2288574Notes

Reaction equation

HRID 2288574 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:15]([CH:16]=1)=[N:14][C:13]1[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=1)[C:7]=2[C:17]([OH:19])=[O:18].N1C=CC=CC=1.F[C:27]1[CH:32]=[CH:31][CH:30]=[C:29](F)[C:28]=1O>S(Cl)(Cl)=O.C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:15]([CH:16]=1)=[N:14][C:13]1[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=1)[C:7]=2[C:17]([O:19][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:18]

Participants

6

Reactant 3

HCID 1049PyridineHCID 943922,6-DifluorophenolHCID 10538808HCID 10538808, compound

Product 1

HCID 18006778HCID 18006778, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent3×HCID 24386Thionyl ChlorideSolvent

Procedure

3-Methoxy-acridine-9-carboxylic acid (0.50 g) was suspended in 10 mL thionyl chloride (3-10 mL) and reaction mixture was refluxed for 3 h. The solvent was removed under reduced pressure to obtain a yellow solid which was dissolved in CH2Cl2 and pyridine (0.44 g) under argon. A solution of 2,6-difluorophenol (0.32 g) in CH2Cl2 was added dropwise. The solution was stirred overnight at room temperature then diluted with more CH2Cl2 (100 mL) and washed with water (3×50 mL) . The organic layer was dried over Na2SO4 and concentrated to obtain the product which was further purified by chromatography on silica gel (30% ethyl acetate/hexane) to yield the pure product as a creamy solid. 1H NMR (acetone-d6) δ 4.08 (s, 3H), 7.39-8.29 (m, 12H).

Workup

  1. customreaction mixture
  2. temperaturewas refluxed for 3 h
  3. customThe solvent was removed under reduced pressure
  4. customto obtain a yellow solid which
  5. washwashed with water (3×50 mL)
  6. dry with materialThe organic layer was dried over Na2SO4
  7. concentrationconcentrated
  8. customto obtain the product which
  9. customwas further purified by chromatography on silica gel (30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-bcee316f12ec493ea0aea5aa24e7fefa
Source dataset
uspto-grants-2000_07
Patent number
US06090571

Reaction notes

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