Nitric Acid → HCID 178466197, compound

HRID 1407180Notes

Reaction equation

HRID 1407180 reaction equation
[CH2:1]([O:3][C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6])[CH3:2].P(=O)(O)(O)O.[N+]([O-])(O)=O.[N:20]([O-])=O.[Na+].C([O-])(=O)C.[K+].[C:29]([CH2:32][C:33](=[O:35])[CH3:34])(=[O:31])[CH3:30]>O.C(O)C>[CH2:1]([O:3][C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH:6][N:20]=[C:32]([C:33](=[O:35])[CH3:34])[C:29](=[O:31])[CH3:30])[CH3:2]

Participants

9

Reactant 6

HCID 944Nitric AcidHCID 1004Phosphoric AcidHCID 7203o-PhenetidineHCID 31261AcetylacetoneHCID 517044Potassium AcetateHCID 23668193Sodium Nitrite

Product 1

HCID 178466197HCID 178466197, compoundYield 55.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

2-Ethoxyaniline (2.00 g, 14.60 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 (1.21 g, 17.52 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 (4.29 g, 43.80 mmol) and acetylacetone (1.90 g, 18.98 mmol) in 60 mL of ethanol and 25 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 (2.00 g, 55% yield): 1H NMR (400 MHz, CDCl3): δ ppm 1.57 (3H, t, J=7.2 Hz), 2.53 (3H, s), 2.63 (3H, s), 4.20 (2H, t, J=7.2 Hz), 7.03-7.07 (1H, m), 7.14-7.18 (1H, m), 7.74-7.84 (2H, m), 14.86 (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-55e3540571c54a38817956f56e1e7e55
Source dataset
uspto-grants-2014_12
Patent number
US08916566B2

Reaction notes

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