Ethyl Acetate → 4-Methyl-5-nitro-2-(1H-1,2,4-triazol-1-yl)pyridine

HRID 580847Notes

Reaction equation

HRID 580847 reaction equation
[NH:1]1[CH:5]=[N:4][CH:3]=[N:2]1.C(=O)([O-])[O-].[K+].[K+].Cl[C:13]1[CH:18]=[C:17]([CH3:19])[C:16]([N+:20]([O-:22])=[O:21])=[CH:15][N:14]=1.C(OCC)(=O)C>CN(C=O)C.O>[CH3:19][C:17]1[C:16]([N+:20]([O-:22])=[O:21])=[CH:15][N:14]=[C:13]([N:1]2[CH:5]=[N:4][CH:3]=[N:2]2)[CH:18]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 3453642-Chloro-4-methyl-5-nitropyridine

Product 1

HCID 542579534-Methyl-5-nitro-2-(1H-1,2,4-triazol-1-yl)pyridineYield 43%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1,2,4-triazole (4.0 g, 58 mmol) in dry DMF (20 mL) was added potassium carbonate (12.0 g, 87 mmol) and 2-chloro-4-methyl-5-nitropyridine (10 g, 58 mmol) and the mixture stirred at ambient temperature under nitrogen for 24 hours. Ethyl acetate (500 mL) and water (250 mL) were added to the mixture and the resulting precipitate was collected by filtration to give the title compound (5.08 g, 43%) as a pale brown solid. The filtrate was separated and the organic phase was washed with water (250 mL) and brine (250 mL), dried (MgSO4) and evaporated. The residue was triturated with ethyl acetate and the precipitate collected by filtration to give the title compound as a brown solid (4.11 g, 35%, overall yield 78%). mp 198-200° C. 1H NMR (360 MHz, CDCl3) δ 2.72 (3H, s), 7.86 (1H, s), 8.07 (1H, s) 9.03 (1H, s) and 9.15 (1H, s).

Workup

  1. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-df1f92038f3c46ae88a6180b09be646a
Source dataset
uspto-grants-1999_07
Patent number
US05919783

Reaction notes

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