Ethyl Acetate → HCID 22141383, compound

HRID 1826220Notes

Reaction equation

HRID 1826220 reaction equation
C[O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH3:18])=[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[NH:9]2)=[CH:5][CH:4]=1.Cl.N1C=CC=CC=1.C(OCC)(=O)C>O>[OH:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH3:18])=[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[NH:9]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 10176127Pyridinium chlorideHCID 22141379HCID 22141379, compound

Product 1

HCID 22141383HCID 22141383, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6-Methoxy-3-methyl-2-phenyl-1H-indole (5.00 g; synthesized according to the process described in Tetrahedron, vol. 41, p. 4615 (1985)) and pyridine hydrochloride (11.56 g) were stirred at 180° C. for 100 minutes. After the reaction mixture was cooled down to room temperature, ethyl acetate and water were added. After the layers were separated, the organic layer was washed sequentially with aqueous 0.5 N hydrochloric acid and saturated brine, and dried. The solvent was then distilled off under reduced pressure. The residue was purified by silica gel column chromatography to yield the title compound (4.50 g).

Workup

  1. customsynthesized
  2. customAfter the layers were separated
  3. washthe organic layer was washed sequentially with aqueous 0.5 N hydrochloric acid and saturated brine
  4. customdried
  5. distillationThe solvent was then distilled off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b0345b28439a4863aa2a1d654796908a
Source dataset
uspto-grants-2006_05
Patent number
US07049445B2

Reaction notes

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