Ammonium Chloride → 5-(5-(2-Fluorocyclopropyl)-1,2,4-oxadiazol-3-yl)-2-methylaniline

HRID 1497900Notes

Reaction equation

HRID 1497900 reaction equation
[F:1][CH:2]1[CH2:4][CH:3]1[C:5]1[O:9][N:8]=[C:7]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[C:12]([N+:17]([O-])=O)[CH:11]=2)[N:6]=1.[Cl-].[NH4+]>CCO.O.[Zn]>[F:1][CH:2]1[CH2:4][CH:3]1[C:5]1[O:9][N:8]=[C:7]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[C:12]([CH:11]=2)[NH2:17])[N:6]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 712807295-(2-Fluorocyclopropyl)-3-(4-methyl-3-nitrophenyl)-1,2,4-oxadiazole

Product 1

HCID 866775315-(5-(2-Fluorocyclopropyl)-1,2,4-oxadiazol-3-yl)-2-methylaniline

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 19096565Water ethanolSolvent

Conditions

Temperature
85 °C

Procedure

To a suspension of 5-(2-fluorocyclopropyl)-3-(4-methyl-3-nitrophenyl)-1,2,4-oxadiazole (129) (162 mg, 0.62 mmol) in EtOH:H2O (4:1) (3.3 mL) was added zinc dust (161 mg, 2.46 mmol) and ammonium chloride (132 mg, 2.46 mmol). The reaction mixture was heated at 85° C. for 24 hours, then filtered hot over celite and rinsed with ethyl acetate. The solvent was concentrated to give 5-(5-(2-fluorocyclopropyl)-1,2,4-oxadiazol-3-yl)-2-methylaniline (130).

Workup

  1. filtrationfiltered hot over celite
  2. washrinsed with ethyl acetate
  3. concentrationThe solvent was concentrated

Sources & evidence

ORD record
ord-c12c17b075e34b5e819a248425bfcc4d
Source dataset
uspto-grants-2015_12
Patent number
US09199981B2

Reaction notes

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