Nitric Acid → HCID 178468353, compound

HRID 1407189Notes

Reaction equation

[N:1]1([C:6]2[CH:12]=[CH:11][C:9]([NH2:10])=[CH:8][CH:7]=2)[CH:5]=[N:4][CH:3]=[N:2]1.P(=O)(O)(O)O.[N+]([O-])(O)=O.[N:22]([O-])=O.[Na+].[CH3:26][C:27](=[O:32])[CH2:28][C:29](=[O:31])[CH3:30].C([O-])(=O)C.[K+].C([O-])([O-])=O.[Na+].[Na+]>C(O)C>[N:1]1([C:6]2[CH:12]=[CH:11][C:9]([NH:10][N:22]=[C:28]([C:27](=[O:32])[CH3:26])[C:29](=[O:31])[CH3:30])=[CH:8][CH:7]=2)[CH:5]=[N:4][CH:3]=[N:2]1

Participants

Conditions

Temperature: -6 °C

Procedure

4-(1H-1,2,4-Triazol-1-yl)aniline (500 mg, 3.12 mmol) was added to a solution of 3 mL of phosphoric acid (85%) and 2 mL of nitric acid (65%) at −6° C. When the mixture reached to room temperature, it was cooled to −6° C. and sodium nitrite (216 mg, 3.12 mmol) was added during 10 min. Small piece of ice (50 g) was added into the solution. The mixture was added at 0° C. to a suspension of 2,4-pentanedione (312 mg, 3.12 mmol) and potassium acetate (20 g) in ethanol (250 mL). The solution was stirred for 15 min, and then was added to 250 mL of saturated Na2CO3 aqueous solution, extracted with dichloromethane, washed with water and brine, dried over Na2SO4, and concentrated under reduced pressure to give the title compound (600 mg, 71% yield) as a brown solid: 1H NMR (400 MHz, CDCl3): δ ppm 2.54 (3H, s), 2.63 (3H, s), 7.55 (2H, d, J=8.8 Hz), 7.74 (2H, d, J=8.8 Hz), 8.12 (1H, s), 8.54 (1H, s), 14.76 (1H, s).

Workup

customreached to room temperature
extractionextracted with dichloromethane
washwashed with water and brine
dry with materialdried over Na2SO4
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-2bba40e01cda4272ba01be51532a68e1
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08916566B2

Reaction notes

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