Pyridine-2-carbonitrile → HCID 54759228, compound

HRID 883515Notes

Reaction equation

HRID 883515 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1)#[N:2].[NH2:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]#[N:17])=[N:14][CH:15]=1.O.[NH2:19][NH2:20]>>[N:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[C:1]1[NH:20][N:19]=[C:16]([C:13]2[N:14]=[CH:15][C:10]([NH2:9])=[CH:11][CH:12]=2)[NH:17][N:2]=1

Participants

4

Reactant 3

HCID 7522Pyridine-2-carbonitrileHCID 24654Hydrazine hydrate (1:1)HCID 38713955-Aminopyridine-2-carbonitrile

Product 1

HCID 54759228HCID 54759228, compoundYield 31.3%

Conditions

Temperature
90 °C

Procedure

A dry round-bottom flask was charged with 2-cyanopyridine (0.500 g, 4.8 mmol), 5-amino-2-cyanopyridine (0.572 g, 4.8 mmol), and 64% aqueous hydrazine hydrate (0.932 mL, 19.2 mmol). The flask was fitted with a reflux condenser, and the mixture was heated to 90° C. for 12 hr. The reaction mixture was cooled to room temperature. The resulting orange precipitate was isolated by filtration, washed with cold H2O, and dried under vacuum. The crude orange solid was concentrated in vacuo onto deactivated silica gel and chromatographed using a gradient (0-60%) of acetone in hexanes to give 377 mg (1.5 mmol, 31%) of 6-(6-pyridin-2-yl-1,4-dihydro-[1,2,4,5]tetrazin-3-yl)-pyridin-3-ylamine as an orange solid, mp 158-160° C.

Workup

  1. customThe flask was fitted with a reflux condenser
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customThe resulting orange precipitate was isolated by filtration
  4. washwashed with cold H2O
  5. customdried under vacuum
  6. concentrationThe crude orange solid was concentrated in vacuo
  7. customchromatographed

Sources & evidence

ORD record
ord-f118bb497b0c474ca5afb61dea494073
Source dataset
uspto-grants-2012_08
Patent number
US08236949B2

Reaction notes

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