Nitric Acid → HCID 178468310, compound

HRID 1407177Notes

Reaction equation

HRID 1407177 reaction equation
[CH3:1][CH:2]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6])[CH3:3].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>[CH3:1][CH:2]([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])[CH3:3]

Participants

9

Reactant 6

HCID 944Nitric AcidHCID 1004Phosphoric AcidHCID 125612-IsopropylanilineHCID 31261AcetylacetoneHCID 517044Potassium AcetateHCID 23668193Sodium Nitrite

Product 1

HCID 178468310HCID 178468310, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

2-(1-Methylethyl)aniline (2.00 g, 14.81 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 (1.23 g, 17.78 mmol) in 4 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 (4.35 g, 44.43 mmol) and acetylacetone (1.92 g, 19.25 mmol) in 80 mL of ethanol and 20 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 (0.98 g, 27% yield): 1H NMR (400 MHz, CDCl3): δ ppm 1.34 (6H, d, J=6.8 Hz), 2.52 (3H, s), 2.63 (3H, s), 3.12-3.21 (1H, m), 7.19-7.23 (1H, m), 7.28-7.34 (2H, m), 7.77-8.00 (1H, m), 15.23 (1H, brs).

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-e02b27ddfe2b4a61975d62ede7266677
Source dataset
uspto-grants-2014_12
Patent number
US08916566B2

Reaction notes

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