Nitric Acid → HCID 178468322, compound

HRID 1407181Notes

Reaction equation

HRID 1407181 reaction equation
[CH3:1][CH:2]([O:4][C:5]1[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=1[NH2:7])[CH3:3].P(=O)(O)(O)O.[N+]([O-])(O)=O.[N:21]([O-])=O.[Na+].C([O-])(=O)C.[K+].[C:30]([CH2:33][C:34](=[O:36])[CH3:35])(=[O:32])[CH3:31]>O.C(O)C>[CH3:3][CH:2]([O:4][C:5]1[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=1[NH:7][N:21]=[C:33]([C:34](=[O:36])[CH3:35])[C:30](=[O:32])[CH3:31])[CH3:1]

Participants

9

Reactant 6

HCID 944Nitric AcidHCID 1004Phosphoric AcidHCID 31261AcetylacetoneHCID 344362-(1-Methylethoxy)benzenamineHCID 517044Potassium AcetateHCID 23668193Sodium Nitrite

Product 1

HCID 178468322HCID 178468322, compoundYield 30.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

2-(1-Methylethoxy)aniline (1.00 g, 6.62 mmol) was added to a solution of 6 mL of phosphoric acid (85%) and 4 mL of nitric acid (65%) at −6° C., followed by sodium nitrite (0.55 g, 7.95 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 solution of potassium acetate (1.95 g, 19.86 mmol) and acetylacetone (0.86 g, 8.61 mmol) in 40 mL of ethanol and 10 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 (0.53 g, 30% yield): 1H NMR (400 MHz, CDCl3): δ ppm 1.28-1.41 (6H, m), 2.50 (3H, s), 2.63 (3H, s), 4.53-4.59 (1H, m), 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-6fc5c93c98f245e19ffd4e054ddbff95
Source dataset
uspto-grants-2014_12
Patent number
US08916566B2

Reaction notes

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