Nitric Acid → HCID 178468357, compound

HRID 1407190Notes

Reaction equation

HRID 1407190 reaction equation
[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1.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:10]=[CH:9][C:7]([NH:8][N:22]=[C:34]([C:35](=[O:37])[CH3:36])[C:31](=[O:33])[CH3:32])=[CH:6][CH:5]=1

Participants

9

Reactant 6

HCID 944Nitric AcidHCID 1004Phosphoric AcidHCID 31261AcetylacetoneHCID 517044Potassium AcetateHCID 6008484-(Trifluoromethoxy)anilineHCID 23668193Sodium Nitrite

Product 1

HCID 178468357HCID 178468357, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

4-(Trifluoromethoxy)aniline (1.00°g, 6.9 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 (0.601 g, 8.7 mmol, 1.2 equiv.) 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 mixture of potassium acetate (2.028 g, 20.7 mmol, 3.0 equiv.) and acetylacetone (0.8 mL, 7.0 mmol, 1.0 equiv.) in 20 mL of ethanol. The mixture was stirred at room temperature for 15 min, filtered, extract with AcOEt, washed with brine and dried to give crude product (1.58 g, 88% yield), which was used directly to the next step. 1H NMR (400 MHz, CDCl3): δ ppm 2.50 (s, 3H), 2.61 (s, 3H), 7.26-7.28 (m, 2H), 7.40-7.43 (m, 2H), 14.69 (s, 1H).

Workup

  1. additionThen to the reaction mixture was added dropwise
  2. stirringThe mixture was stirred at room temperature for 15 min
  3. filtrationfiltered
  4. extractionextract with AcOEt
  5. washwashed with brine
  6. customdried

Sources & evidence

ORD record
ord-0563125dd45544148bc0c996e12a806b
Source dataset
uspto-grants-2014_12
Patent number
US08916566B2

Reaction notes

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