Nitric Acid → HCID 178468315, compound
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-02955077bac14e90828a86199dae1247
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08354411B2
Reaction notes
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