Nitric Acid → HCID 178468315, compound

HRID 1407178Notes

Reaction equation

HRID 1407178 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

9

Reactant 6

HCID 944Nitric AcidHCID 1004Phosphoric AcidHCID 31261AcetylacetoneHCID 729132-AminobenzonitrileHCID 517044Potassium AcetateHCID 23668193Sodium Nitrite

Product 1

HCID 178468315HCID 178468315, compoundYield 41.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

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

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

Sources & evidence

ORD record
ord-e95a38830879445b9ca6679665a54916
Source dataset
uspto-grants-2014_12
Patent number
US08916566B2

Reaction notes

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