Nitric Acid → HCID 178468351, compound

HRID 1895196Notes

Reaction equation

[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:14]=[CH:13][C:11]([NH2:12])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.P(=O)(O)(O)O.[N+]([O-])(O)=O.[N:24]([O-])=O.[Na+].[CH3:28][C:29](=[O:34])[CH2:30][C:31](=[O:33])[CH3:32].C([O-])(=O)C.[K+].C([O-])([O-])=O.[Na+].[Na+]>C(O)C>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:8]2[CH:14]=[CH:13][C:11]([NH:12][N:24]=[C:30]([C:29](=[O:34])[CH3:28])[C:31](=[O:33])[CH3:32])=[CH:10][CH:9]=2)[CH2:6][CH2:7]1

Participants

Conditions

Temperature: -6 °C

Procedure

4-(4-Methylpiperazin-1-yl)aniline (1000 mg, 5.24 mmol) was added to a solution of 6 mL of phosphoric acid (85%) and 4 mL of nitric acid (65%) at −6° C. When the mixture reached to room temperature, it was cooled to −6° C. and sodium nitrite (361 mg, 5.24 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 (524 mg, 5.24 mmol) and potassium acetate (30 g) in ethanol (400 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 (610 mg, 39% yield): 1H NMR (400 MHz, CDCl3): δ ppm 2.40 (3H, s), 2.50 (3H, s), 2.62 (3H, s), 3.10 (4H, t, J=5.2 Hz), 3.25 (4H, t, J=4.8 Hz), 7.30 (2H, d, J=8.8 Hz), 7.37 (2H, d, J=7.6 Hz), 15.08 (1H, brs).

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-e99d9fa6184d49db8538f24a82c8436d
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08513251B2

Reaction notes

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