Nitric Acid → HCID 178468315, compound

HRID 1624658Notes

Reaction equation

[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].P(=O)(O)(O)O.[N+]([O-])(O)=O.[N:19]([O-])=O.[Na+].C([O-])(=O)C.[K+].[C:28]([CH2:31][C:32](=[O:34])[CH3:33])(=[O:30])[CH3:29]>O.C(O)C>[C:28]([C:31](=[N:19][NH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5])[C:32](=[O:34])[CH3:33])(=[O:30])[CH3:29]

Participants

Conditions

Temperature: 0 °C

Procedure

2-Aminobenzonitrile (5.00 g, 42.37 mmol) was added to a solution of 30 mL of phosphoric acid (85%) and 20 mL of nitric acid (65%) at −6° C., followed by sodium nitrite (3.50 g, 50.78 mmol) in 10 mL of water dropwise at 0° C., and the mixture was stirred at 0° C. for 30 min. Then, to the reaction mixture was added dropwise a solution of potassium acetate (12.45 g, 127.11 mmol) and acetylacetone (5.51 g, 55.08 mmol) in 80 mL of ethanol and 48 mL of water. The mixture was stirred at room temperature overnight, filtered, washed with water, EtOH/H2O (1/1) and hexane, and dried to give the title compound (4.00 g, 41% yield): 1H NMR (400 MHz, CDCl3): δ ppm 2.50 (3H, s), 2.63 (3H, s), 7.21-7.25 (1H, m), 7.62-7.66 (2H, m), 7.77-7.79 (1H, m), 15.01 (1H, s).

Workup

stirringThe mixture was stirred at room temperature overnight
filtrationfiltered
washwashed with water, EtOH/H2O (1/1) and hexane
customdried

Sources & evidence

ORD record: ord-99db81a871414626a51cc7e3370f00b2
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778944B2

Reaction notes

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