Hydrazine hydrate (1:1) → 6-(1H-1,2,4-Triazol-1-yl)pyridin-3-amine

HRID 926735Notes

Reaction equation

HRID 926735 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH:14]=[N:13][CH:12]=[N:11]2)=[N:8][CH:9]=1)([O-])=O.O.NN>[Ni].C(O)C.CO>[N:10]1([C:7]2[N:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=2)[CH:14]=[N:13][CH:12]=[N:11]1

Participants

6

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 27667645-nitro-2-(1H-1,2,4-triazol-1-yl)pyridine

Product 1

HCID 167723276-(1H-1,2,4-Triazol-1-yl)pyridin-3-amine

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

Raney nickel (0.650 g) was added to a solution of 5-nitro-2-(1H-1,2,4-triazol-1-yl)pyridine (3.2 g, 16.7 mmol) in a mixture of ethanol and methanol (1:1) (150 mL) followed by the addition of Hydrazine hydrate (2.51 g, 50.2 mmol) and stirring was continued at 25° C. 1 hr. The reaction mixture was filtered over celite bed and washed with methanol. The filtrate and the washings were concentrated under reduced pressure to afford title compound as pale brown liquid. MS (ESI): m/z 162.1 (M+H).

Workup

  1. customwas continued at 25° C
  2. custom1 hr
  3. filtrationThe reaction mixture was filtered over celite bed
  4. washwashed with methanol
  5. concentrationThe filtrate and the washings were concentrated under reduced pressure

Sources & evidence

ORD record
ord-e0ba472449004b1f9bcbfae8f21479ea
Source dataset
uspto-grants-2016_03
Patent number
US09289419B2

Reaction notes

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