Water → HCID 18696609, compound

HRID 1870551Notes

Reaction equation

HRID 1870551 reaction equation
[Cl:1][C:2]1[N:3]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([O:19]C)[CH:17]=3)[CH:12]=[CH:11][CH:10]=2)[C:4](=[O:8])[N:5]([CH3:7])[N:6]=1.[Cl-].[Cl-].[Cl-].[Al+3].O>C(Cl)Cl>[Cl:1][C:2]1[N:3]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([OH:19])[CH:17]=3)[CH:12]=[CH:11][CH:10]=2)[C:4](=[O:8])[N:5]([CH3:7])[N:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6451240Aluminum(III) ChlorideHCID 18696597HCID 18696597, compound

Product 1

HCID 18696609HCID 18696609, compoundYield 79.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the title compound of Step E (2.9 g) in methylene chloride (35 mL) was cooled to 0° C. while stirring under N2, and aluminum trichloride (4.0 g) was added in portions. The reaction mixture was allowed to warm to room temperature and then was heated to reflux for 18 h. The reaction mixture was cooled to room temperature, poured into water and extracted with ethyl acetate. The combined organic extracts were dried (MgSO4), filtered and concentrated under reduced pressure. The crude material was purified by flash chromatography (1:4 ethyl acetate:hexane as eluent) to afford 2.2 g of the title compound of Step F. 1H NMR (Me2SO-d6): δ 10.08 (s,1H), 8.02 (d,1H), 7.95 (d,1H), 7.59 (dd,1H), 7.41 (t,1H), 7.18 (dd,1H), 6.71 (d,1H), 3.49 (s,3H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 18 h
  3. temperatureThe reaction mixture was cooled to room temperature
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude material was purified by flash chromatography (1:4 ethyl acetate:hexane as eluent)

Sources & evidence

ORD record
ord-a21c742b01174686bba75d37598d444c
Source dataset
uspto-grants-2000_08
Patent number
US06096895

Reaction notes

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