Hydrochloric Acid → 3-(5-Methyl-1,3,4-oxadiazol-2-yl)aniline

HRID 621469

Reaction equation

HRID 621469 reaction equation
[CH3:1][C:2]1[O:3][C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-])=O)[CH:8]=2)=[N:5][N:6]=1.Cl.[OH-].[K+]>C(O)C.[Fe]>[CH3:1][C:2]1[O:3][C:4]([C:7]2[CH:8]=[C:9]([NH2:13])[CH:10]=[CH:11][CH:12]=2)=[N:5][N:6]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 28063312-Methyl-5-(3-nitrophenyl)-1,3,4-oxadiazole

Product 1

HCID 144076283-(5-Methyl-1,3,4-oxadiazol-2-yl)anilineYield 75.9%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent2×

Procedure

Iron powder, 27.9 g (0.5 mol), is added to a mixture of 2-methyl-5-(3-nitrophenyl)-1,3,4-oxadiazole, (0.053 mol), in 1000 ml of ethyl alcohol with stirring. The mixture is heated to reflux and 1.73 ml of concentrated hydrochloric acid in 10 ml of ethyl alcohol is added dropwise. The mixture is reluxed three hours, 20 ml of 1 normal potassium hydroxide is added, the mixture filtered, and the filtrate evaporated. The residue is dissolved in dichloromethane, washed with water, and the methylene chloride layer separated and evaporated to give 7.05 g of 3-(5-methyl-1,3,4-oxadiazol-2-yl) benzenamine after recrystallization from 2-propanol; mp 139°-140° C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux
  3. filtrationthe mixture filtered
  4. customthe filtrate evaporated
  5. dissolutionThe residue is dissolved in dichloromethane
  6. washwashed with water
  7. customthe methylene chloride layer separated
  8. customevaporated

Sources & evidence

ORD record
ord-9d551c2f419f4bf89e8d960da84a2458
Source dataset
uspto-grants-1989_04
Patent number
US04824843

Linked notes

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