Nitric Acid → HCID 178468357, compound

HRID 1624670Notes

Reaction equation

HRID 1624670 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-4c772b456e1148638fdf7b269a7207ce
Source dataset
uspto-grants-2014_07
Patent number
US08778944B2

Reaction notes

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