HCID 20458183, compound → HCID 20458180, compound

HRID 544718Notes

Reaction equation

HRID 544718 reaction equation
[Cl:1][C:2]1[C:3]([N:13](CC2C=CC=CC=2)CC2C=CC=CC=2)=[CH:4][C:5]2[O:9][C:8](=[O:10])[CH:7]([CH3:11])[C:6]=2[CH:12]=1.[H][H]>O1CCOCC1.[Pd]>[NH2:13][C:3]1[C:2]([Cl:1])=[CH:12][C:6]2[CH:7]([CH3:11])[C:8](=[O:10])[O:9][C:5]=2[CH:4]=1

Participants

5

Reactant 2

HCID 20458183HCID 20458183, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20458180HCID 20458180, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of 21.8 g (0.058 mole) of 5-chloro-6-dibenzylamino-3-methylbenzofuran-2(3H)-one in 220 ml of dioxane is reduced with 2.0 g of palladium-on-carbon (5% strength) at room temperature with hydrogen without superatmospheric pressure. After absorption of the theoretical amount of hydrogen the catalyst is removed by filtration and the dioxane is evaporated off in vacuo. 20 ml of cold methanol are added to the residue and the precipitate is filtered off. 6-amino-5-chloro-3-methylbenzofuran-2(3H)-one is obtained in the form of colourless crystals having a melting point of 139°-140°.

Workup

  1. customAfter absorption of the theoretical amount of hydrogen the catalyst
  2. customis removed by filtration
  3. customthe dioxane is evaporated off in vacuo
  4. addition20 ml of cold methanol are added to the residue
  5. filtrationthe precipitate is filtered off

Sources & evidence

ORD record
ord-43b55502adcf405fa27902b471e2f17b
Source dataset
uspto-grants-1984_05
Patent number
US04451462

Reaction notes

Loading…