1-(4-Methyl-3-nitrophenoxy)propan-2-one → HCID 20255642, compound

HRID 637692Notes

Reaction equation

HRID 637692 reaction equation
[CH3:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][CH2:7][C:8](=O)[CH3:9])=[CH:4][C:3]=1[N+:13]([O-])=O>[Pd].O1CCOCC1>[NH2:13][C:3]1[C:2]([CH3:1])=[CH:12][C:11]2[C:8]([CH3:9])=[CH:7][O:6][C:5]=2[CH:4]=1

Participants

4

Reactant 1

HCID 202556351-(4-Methyl-3-nitrophenoxy)propan-2-one

Product 1

HCID 20255642HCID 20255642, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 96.2 g (0.46 mole) of 1-(4-methyl-3-nitrophenoxy)-2-propanone, 10 g of 5% palladium on carbon and 960 ml of dioxane is hydrogenated for 6 hours at room temperature. The catalyst is subsequently filtered off and the filtrate is concentrated by evaporation in vacuo. The resulting residue is taken up in 2.5 liters of ethanol, 400 ml of concentrated hydrochloric acid are added and the whole is boiled under reflux for 30 hours. The ethanol is removed in vacuo and the residue is diluted with ice-water, rendered alkaline with 6N sodium hydroxide solution and extracted with ether. The crude product obtained after drying and concentration by evaporation of the organic phase is chromatographed over silica gel with methylene chloride/acetone. Recrystallisation of the pure fractions from petroleum ether yields 6-amino-3,5-dimethylbenzofuran having a melting point of 64°-65°.

Workup

  1. filtrationThe catalyst is subsequently filtered off
  2. concentrationthe filtrate is concentrated by evaporation in vacuo
  3. addition400 ml of concentrated hydrochloric acid are added
  4. temperatureunder reflux for 30 hours
  5. customThe ethanol is removed in vacuo
  6. additionthe residue is diluted with ice-water
  7. extractionextracted with ether
  8. customThe crude product obtained
  9. customafter drying
  10. concentrationconcentration
  11. customby evaporation of the organic phase
  12. customis chromatographed over silica gel with methylene chloride/acetone
  13. customRecrystallisation of the pure fractions from petroleum ether

Sources & evidence

ORD record
ord-dbaa3087899e4b139fbcf5dd5231e901
Source dataset
uspto-grants-1985_12
Patent number
US04558043

Reaction notes

Loading…