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

HRID 2167797

Reaction equation

HRID 2167797 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-144c7b6f515b41598b22ac4f6e0f72af
Source dataset
uspto-grants-2015_06
Patent number
US09045479B2

Linked notes

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