Nitric Acid → HCID 178468339, compound

HRID 1407084Notes

Reaction equation

[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.P(=O)(O)(O)O.[N+]([O-])(O)=O.[N:19]([O-])=O.[Na+].[CH3:23][C:24](=[O:29])[CH2:25][C:26](=[O:28])[CH3:27].C([O-])(=O)C.[K+].C([O-])([O-])=O.[Na+].[Na+]>C(O)C>[C:26]([C:25](=[N:19][NH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1)[C:24](=[O:29])[CH3:23])(=[O:28])[CH3:27]

Participants

Conditions

Temperature: -6 °C

Procedure

4-Aminobenzonitrile (500 mg, 4.24 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 solid sodium nitrite (292 mg, 4.24 mmol) was added during 10 min. Small pieces of ice (50 g) were added into the solution. The mixture was added at 0° C. to a suspension of corresponding 2,4-pentanedione (424 mg, 4.24 mmol) and potassium acetate (20 g) in ethanol (250 mL). The solution was stirred for 15 min, 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 4-[2-(1-acetyl-2-oxopropylidene)hydrazino]benzonitrile (280 mg, 29%).

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-3ff6015836124de4bd4fd941ff7d62c3
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08916566B2

Reaction notes

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