Ammonium Chloride → 2-PyridinaMine, 5-(1H-tetrazol-5-yl)-

HRID 1927270Notes

Reaction equation

HRID 1927270 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[N:9])=[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:5]1[CH:6]=[CH:7][C:2]([NH2:1])=[N:3][CH:4]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 8182602-Amino-5-cyanopyridine

Product 2

HCID 222AmmoniaHCID 587726282-PyridinaMine, 5-(1H-tetrazol-5-yl)-Yield 126.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Amino-5-cyanopyridine (1.0 g), sodium azide (1.1 g), ammonium chloride (890 mg), and DMF (15 mL) were stirred for 2 hours and 15 minutes at 100° C. The reaction solution was directly purified by silica gel chromatography (ethyl acetate, then ethyl acetate:methanol:concentrated aqueous ammonia=6:2:1) to obtain the titled compound (860 mg).

Workup

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

Sources & evidence

ORD record
ord-98006bfa3bb84f6aa5ff7597352bc58e
Source dataset
uspto-grants-2012_05
Patent number
US08183264B2

Reaction notes

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