Nitric Acid → HCID 178468340, compound

HRID 1624568Notes

Reaction equation

[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=1.P(=O)(O)(O)O.[N+]([O-])(O)=O.[N:20]([O-])=O.[Na+].[CH3:24][C:25](=[O:30])[CH2:26][C:27](=[O:29])[CH3:28].C([O-])(=O)C.[K+].C([O-])([O-])=O.[Na+].[Na+]>C(O)C>[C:27]([C:26](=[N:20][NH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=1)[C:25](=[O:30])[CH3:24])(=[O:29])[CH3:28]

Participants

Conditions

Temperature: -6 °C

Procedure

4-Aminobenzamide (1000 mg, 7.36 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 solid sodium nitrite (508 mg, 7.36 mmol) was added during 10 min. Small pieces of ice (100 g) were added into the solution. The mixture was added at 0° C. to a suspension of corresponding 2,4-pentanedione (736 mg, 7.36 mmol) and potassium acetate (40 g) in ethanol (400 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]benzamide (460 mg, 25%).

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-da3de6ef00c546da90f84a28aab68247
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778944B2

Reaction notes

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