Nitric Acid → HCID 178468320, compound

HRID 1805544Notes

Reaction equation

HRID 1805544 reaction equation
[O:1]([C:8]1[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=1[NH2:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(=O)(O)(O)O.[N+]([O-])(O)=O.[N:24]([O-])=O.[Na+].C([O-])(=O)C.[K+].[C:33]([CH2:36][C:37](=[O:39])[CH3:38])(=[O:35])[CH3:34]>O.C(O)C>[O:1]([C:8]1[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=1[NH:10][N:24]=[C:36]([C:37](=[O:39])[CH3:38])[C:33](=[O:35])[CH3:34])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

9

Reactant 6

HCID 944Nitric AcidHCID 1004Phosphoric AcidHCID 31261AcetylacetoneHCID 75899Benzenamine, 2-phenoxy-HCID 517044Potassium AcetateHCID 23668193Sodium Nitrite

Product 1

HCID 178468320HCID 178468320, compoundYield 31.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

2-Phenoxyaniline (2.00 g, 10.81 mmol) was added to a solution of 12 mL of phosphoric acid (85%) and 8 mL of nitric acid (65%) at −6° C., followed by sodium nitrite (0.90 g, 12.97 mmol) in 2 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 mixture of potassium acetate (3.18 g, 32.43 mmol) and acetylacetone (1.40 g, 14.05 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 (1.00 g, 31% yield): 1H NMR (400 MHz, CDCl3): δ ppm 2.50 (3H, s), 2.63 (3H, s), 7.26-7.88 (9H, m), 14.91 (1H, s).

Workup

  1. additionThen, to the reaction mixture was added dropwise
  2. stirringThe mixture was stirred at room temperature overnight
  3. filtrationfiltered
  4. washwashed with water, EtOH/H2O (1/1) and hexane
  5. customdried

Sources & evidence

ORD record
ord-d00e2a072f0541ff8f6428d9a85c9f77
Source dataset
uspto-grants-2013_01
Patent number
US08354411B2

Reaction notes

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