1-[3-(4-nitro-phenoxy)-propyl]-1H-[1,2,3]triazole → 4-(3-[1,2,3]Triazol-1-yl-propoxy)-phenylamine

HRID 1271413Notes

Reaction equation

HRID 1271413 reaction equation
[N+:1]([C:4]1[CH:18]=[CH:17][C:7]([O:8][CH2:9][CH2:10][CH2:11][N:12]2[CH:16]=[CH:15][N:14]=[N:13]2)=[CH:6][CH:5]=1)([O-])=O>C1COCC1.[Pd]>[N:12]1([CH2:11][CH2:10][CH2:9][O:8][C:7]2[CH:6]=[CH:5][C:4]([NH2:1])=[CH:18][CH:17]=2)[CH:16]=[CH:15][N:14]=[N:13]1

Participants

4

Reactant 1

HCID 184535181-[3-(4-nitro-phenoxy)-propyl]-1H-[1,2,3]triazole

Product 1

HCID 184535284-(3-[1,2,3]Triazol-1-yl-propoxy)-phenylamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

1-[3-(4-Nitro-phenoxy)-propyl]-1H-[1,2,3]triazole (2.87 g, 11.6 mmol) is dissolved in THF (40 ml) and hydrogenated for 2.5 h in the presence of palladium on charcoal (10%, 500 mg). After filtration and concentration in vacuo 4-(3-[1,2,3]Triazol-1-yl-propoxy)-phenylamine can be isolated as orange oil which is precipitated with diethyl ether. Yield 2.48 g (98%)

Workup

  1. filtrationAfter filtration and concentration in vacuo 4-(3-[1,2,3]Triazol-1-yl-propoxy)-phenylamine
  2. customcan be isolated as orange oil which
  3. customis precipitated with diethyl ether

Sources & evidence

ORD record
ord-a2fd757ed50d42b790a80a504b568d8a
Source dataset
uspto-grants-2007_04
Patent number
US07205326B2

Reaction notes

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