HCID 20472059, compound → HCID 13067095, compound

HRID 2296312Notes

Reaction equation

HRID 2296312 reaction equation
[NH2:1][CH2:2][C:3]1[C:4]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=2[CH:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[F:24])O)=[C:5]([CH3:8])[NH:6][CH:7]=1>O1CCCC1.[O-2].[O-2].[Mn+4]>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]2[C:4]3[C:3](=[CH:7][NH:6][C:5]=3[CH3:8])[CH2:2][N:1]=[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[F:24])[C:10]=2[CH:11]=1

Participants

4

Reactant 1

HCID 20472059HCID 20472059, compound

Product 1

HCID 13067095HCID 13067095, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 150 mg (0.43 mmole) of 4-aminomethyl-3-{4-chloro-2-[(2-fluorophenyl)hydroxymethyl]phenyl}-2-methyl-1H-pyrrole and 600 mg (7.3 mmole) of manganese dioxide in 30 ml of tetrahydrofuran was refluxed for 2 hours. The mixture was cooled and filtered over celite. The filtrate was concentrated at reduced pressure to give an amber oil. Purification by column chromatography (silica gel, 10 g; eluent 5% ether in methylene chloride) gave a cream colored solid. Recrystallization from ether gave colorless needles, mp 226°-227° which was identical in every respect to an authentic sample.

Workup

  1. temperaturewas refluxed for 2 hours
  2. temperatureThe mixture was cooled
  3. filtrationfiltered over celite
  4. concentrationThe filtrate was concentrated at reduced pressure
  5. customto give an amber oil
  6. customPurification by column chromatography (silica gel, 10 g; eluent 5% ether in methylene chloride)
  7. customgave a cream
  8. customRecrystallization from ether
  9. customgave colorless needles, mp 226°-227° which

Sources & evidence

ORD record
ord-2c077019de094f2d926c92eb62065faf
Source dataset
uspto-grants-1984_01
Patent number
US04428879

Reaction notes

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