Nitric Acid → HCID 178468309, compound

HRID 1407179Notes

Reaction equation

HRID 1407179 reaction equation
[C:1]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:2]([NH2:7])=[CH:3][CH:4]=[CH:5][CH:6]=1.P(=O)(O)(O)O.[N+]([O-])(O)=O.[N:23]([O-])=O.[Na+].C([O-])(=O)C.[K+].[C:32]([CH2:35][C:36](=[O:38])[CH3:37])(=[O:34])[CH3:33]>O.C(O)C>[C:1]1([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][N:23]=[C:35]([C:36](=[O:38])[CH3:37])[C:32](=[O:34])[CH3:33]

Participants

9

Reactant 6

HCID 944Nitric AcidHCID 1004Phosphoric AcidHCID 70152-AminobiphenylHCID 31261AcetylacetoneHCID 517044Potassium AcetateHCID 23668193Sodium Nitrite

Product 1

HCID 178468309HCID 178468309, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

Biphenyl-2-amine (500 mg, 2.96 mmol) was added to a solution of 3 mL of phosphoric acid (85%) and 2 mL of nitric acid (65%) at −6° C., followed by sodium nitrite (254 mg, 3.55 mmol) in 1 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 (870 mg, 8.88 mmol) and acetylacetone (385 mg, 3.85 mmol) in 60 mL of ethanol and 32 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 (420 mg, 51% yield): 1H NMR (400 MHz, CDCl3): δ ppm 2.51 (3H, s), 2.52 (3H, s), 7.29-7.60 (9H, m), 14.63 (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-a4dd9b2b9c2643458d6a3a5fc2a5a12f
Source dataset
uspto-grants-2014_12
Patent number
US08916566B2

Reaction notes

Loading…