Ammonium Chloride → 3-(2H-Tetrazol-5-yl)pyridin-2-amine

HRID 1927221Notes

Reaction equation

HRID 1927221 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[N-:10]=[N+:11]=[N-:12].[Na+].[Cl-].[NH4+]>CN(C=O)C>[NH3:1].[N:9]1[NH:10][N:11]=[N:12][C:8]=1[C:7]1[C:2]([NH2:1])=[N:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 8182592-Amino-3-cyanopyridine

Product 2

HCID 222AmmoniaHCID 131016573-(2H-Tetrazol-5-yl)pyridin-2-amineYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Amino-3-cyanopyridine (1.0 g), sodium azide (1.1 g), ammonium chloride (0.89 g), and DMF (15 mL) were stirred for 1.5 hours at 100° C. The reaction solution was directly purified by silica gel chromatography (ethyl acetate, then ethyl acetate:methanol:concentrated aqueous ammonia=6:2:0.5) to obtain the titled compound (0.66 g).

Workup

  1. customThe reaction solution was directly purified by silica gel chromatography (ethyl acetate

Sources & evidence

ORD record
ord-8b6edd4ad69248b780c40b246768fcaf
Source dataset
uspto-grants-2012_05
Patent number
US08183264B2

Reaction notes

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