Ammonia → 6-Phenyl-1,2,4-triazin-5-amine

HRID 396150Notes

Reaction equation

[C:1]1([C:7]2[N:12]=[N:11][CH:10]=[N:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH3:13].[Mn]([O-])(=O)(=O)=O.[K+]>>[C:1]1([C:7]2[N:12]=[N:11][CH:10]=[N:9][C:8]=2[NH2:13])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Reactant 3

HCID 222Ammonia

HCID 516875Potassium Permanganate

HCID 122539936-Phenyl-1,2,4-triazine

Product 1

HCID 64050996-Phenyl-1,2,4-triazin-5-amineYield 50%

Conditions

Temperature: -37 °C

Procedure

To a mixture of 6-phenyl-[1,2,4]triazine (18 g, 115 mmol) in anhydrous liquid ammonia (1 l) under an atmosphere of nitrogen at −37° C. was added in one portion potassium permanganate (22.6 g, 143 mmol). The reaction mixture was stirred at −37° C. for 30 min and then the ammonia evaporated. To the residue was added propan-2-ol (800 ml) and the resulting mixture heated under reflux for 10 min, then filtered through hyflo. The filtrate was evaporated in vacuo. The residue was purified by flash chromatography (SiO2; 4% MeOH in CH2Cl2+0.5% NH3) to afford 9.8 g (57 mmol, 50%) of 6-phenyl-[1,2,4]triazin-5-ylamine as a yellow solid. δH (360 MHz; CDCl3) 5.58 (2H, br s, NH2), 7.51-7.57 (3H, m, aromatics), 7.68-7.72 (2H, m, aromatics), 8.80 (1H, s, triazine H3); m/z (ES+) 173 (M++H, 100%).

Workup

customthe ammonia evaporated
additionTo the residue was added propan-2-ol (800 ml)
temperaturethe resulting mixture heated
temperatureunder reflux for 10 min
filtrationfiltered through hyflo
customThe filtrate was evaporated in vacuo
customThe residue was purified by flash chromatography (SiO2; 4% MeOH in CH2Cl2+0.5% NH3)

Sources & evidence

ORD record: ord-63635316ead64106ad13544d91786c3d
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06608062B1

Reaction notes

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