HCID 67350465, compound → HCID 67351984, compound

HRID 1672849Notes

Reaction equation

HRID 1672849 reaction equation
[CH3:1][N:2]1[N:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-])=O)[CH:8]=2)[O:4][C:3]1=[O:16].[H][H]>CO.C(Cl)(Cl)Cl.[Pd]>[NH2:13][C:9]1[CH:8]=[C:7]([C:5]2[O:4][C:3](=[O:16])[N:2]([CH3:1])[N:6]=2)[CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 2

HCID 67350465HCID 67350465, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 67351984HCID 67351984, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

3-Methyl-5-(3-nitrophenyl)-1,3,4-oxadiazol-2(3H)-one (2.17 g, 9.79 mmol) obtained in Step 2 was dissolved in methanol (60 mL) and chloroform (51 mL), and the mixture was stirred at room temperature for 4 hours under a stream of hydrogen after adding 10% palladium-on-carbon (217 mg, 0.102 mmol). The mixture was further stirred at room temperature for 4 hours under a stream of hydrogen after adding 10% palladium-on-carbon (217 mg, 0.102 mmol). Then, insolubles were separated by filtration through sellite, and the filtrate was concentrated under reduced pressure. The residue was triturated with diethyl ether, and the solid was filtered off and dried to give 5-(3-aminophenyl)-3-methyl-1,3,4-oxadiazol-2(3H)-one (1.49 g, 80%).

Workup

  1. customThen, insolubles were separated by filtration through sellite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was triturated with diethyl ether
  4. filtrationthe solid was filtered off
  5. customdried

Sources & evidence

ORD record
ord-08f3d72f59784b06958dd0b51b846820
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

Loading…