Nitric Acid → HCID 178468352, compound

HRID 1407203Notes

Reaction equation

[N:1]1([C:7]2[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][CH:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.P(=O)(O)(O)O.[N+]([O-])(O)=O.[N:23]([O-])=O.[Na+].[CH3:27][C:28](=[O:33])[CH2:29][C:30](=[O:32])[CH3:31].C([O-])(=O)C.[K+].C([O-])([O-])=O.[Na+].[Na+]>C(O)C>[N:1]1([C:7]2[CH:13]=[CH:12][C:10]([NH:11][N:23]=[C:29]([C:28](=[O:33])[CH3:27])[C:30](=[O:32])[CH3:31])=[CH:9][CH:8]=2)[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1

Participants

Conditions

Temperature: -6 °C

Procedure

4-Morpholin-4-ylaniline (653 mg, 3.67 mmol) was added to a mixture of 3 mL of phosphoric acid (85%) and 2 mL of nitric acid (65%) at −6° C. When the resulting mixture reached to room temperature, it was cooled to −6° C. and sodium nitrite (253 mg, 3.67 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 (367 mg, 3.67 mmol) and potassium acetate (20 g) in ethanol (250 mL). The solution was stirred for 15 min, and then added to 250 mL of saturated Na2CO3 aqueous solution, extracted with dichloromethane, washed with water and brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure to give the title compound (870 mg, 82% yield) as a brown solid: 1H NMR (400 MHz, CDCl3): δ 2.50 (3H, s), 2.61 (3H, s), 3.15-3.18 (4H, m), 3.80-3.83 (4H, m), 6.98-7.03 (2H, m), 7.45-7.50 (2H, m), 14.37 (1H, s).

Workup

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

Sources & evidence

ORD record: ord-50a6b4c0091f42e0ac5d716e7a969e1c
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08916566B2

Reaction notes

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