HCID 21516664, compound → HCID 21516665, compound

HRID 1283817Notes

Reaction equation

HRID 1283817 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[C:11]1[O:15][N:14]=[C:13]([C:16]2[O:17][CH:18]=[CH:19][CH:20]=2)[N:12]=1>C(O)C.Cl.[Pd]>[NH2:8][C:6]1[CH:5]=[CH:4][C:3]([C:11]2[O:15][N:14]=[C:13]([C:16]3[O:17][CH:18]=[CH:19][CH:20]=3)[N:12]=2)=[C:2]([Cl:1])[CH:7]=1

Participants

5

Reactant 1

HCID 21516664HCID 21516664, compound

Product 1

HCID 21516665HCID 21516665, compoundYield 55%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent2×

Procedure

To a slurry of 28.8 g of 5-(2-chloro-4-nitrophenyl)-3-(2-furanyl)-1,2,4-oxadiazole in 600 ml of absolute ethanol and 34 ml of hydrochloric acid is added a slurry of 2.0 g of 10% palladium on charcoal in ethanol. The mixture is hydrogenated in a Parr hydrogenator at 45 p.s.i. for 3 hours. The insoluble amine hydrochloride is filtered and washed with ethanol. The filtrate is concentrated to dryness and the residue and precipitate are combined and treated with a solution of 20% potassium carbonate in the presence of chloroform. The phases are separated and the aqueous phases extracted three times with 300 ml of chloroform. The organic phases are dried over magnesium sulfate, filtered and concentrated to dryness yielding 20 g of crude product. Recrystallization from acetone/water yields 14.2 g of the title compound in 2 crops, melting point 175°-176.5°C.

Workup

  1. filtrationThe insoluble amine hydrochloride is filtered
  2. washwashed with ethanol
  3. concentrationThe filtrate is concentrated to dryness
  4. additiontreated with a solution of 20% potassium carbonate in the presence of chloroform
  5. customThe phases are separated
  6. extractionthe aqueous phases extracted three times with 300 ml of chloroform
  7. dry with materialThe organic phases are dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated to dryness
  10. customyielding 20 g of crude product
  11. customRecrystallization from acetone/water

Sources & evidence

ORD record
ord-da66c77061d94b1caab38ce32af6e65a
Source dataset
uspto-grants-1976_08
Patent number
US03976657

Reaction notes

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