Nitric Acid → HCID 178468343, compound

HRID 2089853Notes

Reaction equation

HRID 2089853 reaction equation
[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][CH:10]=1)[NH2:7].P(=O)(O)(O)O.[N+]([O-])(O)=O.[N:22]([O-])=O.[Na+].C([O-])(=O)C.[K+].[C:31]([CH2:34][C:35](=[O:37])[CH3:36])(=[O:33])[CH3:32]>O.C(O)C>[F:1][C:2]([F:11])([F:12])[O:3][C:4]1[CH:5]=[C:6]([NH:7][N:22]=[C:34]([C:35](=[O:37])[CH3:36])[C:31](=[O:33])[CH3:32])[CH:8]=[CH:9][CH:10]=1

Participants

9

Reactant 6

HCID 944Nitric AcidHCID 1004Phosphoric AcidHCID 31261AcetylacetoneHCID 737533-(Trifluoromethoxy)anilineHCID 517044Potassium AcetateHCID 23668193Sodium Nitrite

Product 1

HCID 178468343HCID 178468343, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

3-(Trifluoromethoxy)aniline (1.00 g, 5.64 mmol) was added to a solution of 0.6 mL of phosphoric acid (85%) and 4 mL of nitric acid (65%) at −6° C., followed by sodium nitrite (389 mg, 5.64 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 (1.66 g, 16.92 mmol) and acetylacetone (564 mg, 5.64 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 (1.2 g, 74% yield): 1H NMR (400 MHz, CDCl3): δ ppm 2.49 (s, 3H), 2.61 (s, 3H), 7.05-7.08 (m, 1H), 7.25-7.27 (m, 1H), 7.32 (s, 1H), 7.42 (t, J=8.0 Hz, 1H), 14.59 (s, 1H).

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-29d8e275a8114a15b793205cec5e12b3
Source dataset
uspto-grants-2013_05
Patent number
US08435995B2

Reaction notes

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