Isopropyl iodide → HCID 13768631, compound

HRID 2290555Notes

Reaction equation

HRID 2290555 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([N:11]2[CH:15]=[CH:14][CH:13]=[CH:12]2)=[C:8]([OH:10])[CH:9]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].I[CH:23]([CH3:25])[CH3:24]>CC(C)=O.C(Cl)Cl>[CH3:24][CH:23]([O:10][C:8]1[CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[CH:6][C:7]=1[N:11]1[CH:12]=[CH:13][CH:14]=[CH:15]1)[CH3:25]

Participants

6

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 7303337HCID 7303337, compound

Product 1

HCID 13768631HCID 13768631, compoundYield 71.1%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 3.6 g (0.02 mole) of 5-nitro-2-(1H-pyrrol-1-yl)phenol and 3.7 g (0.27 mole) of potassium carbonate in 40 ml of acetone was added 4.5 g (0.027 mole) of 2-iodopropane. After complete addition the mixture was stirred at reflux for approximately 16 hours. The reaction mixture was cooled, and the solvent evaporated under reduced pressure to leave a residue. The residue was dissolved in methylene chloride, filtered, and the filtrate evaporated under reduced pressure to leave residue. The residue was purified by column chromatography on silica gel, eluting with toluene, to yield 3.5 g of 1-(1-methylethoxy-4-nitrophenyl)pyrrole (mp 59°-61° C.).

Workup

  1. additionAfter complete addition the mixture
  2. temperatureat reflux for approximately 16 hours
  3. temperatureThe reaction mixture was cooled
  4. customthe solvent evaporated under reduced pressure
  5. customto leave a residue
  6. filtrationfiltered
  7. customthe filtrate evaporated under reduced pressure
  8. customto leave residue
  9. customThe residue was purified by column chromatography on silica gel
  10. washeluting with toluene

Sources & evidence

ORD record
ord-076a1fda08984534970f6295fbc3ec7e
Source dataset
uspto-grants-1986_10
Patent number
US04617316

Reaction notes

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