Nitric Acid → HCID 59800724, compound

HRID 656712Notes

Reaction equation

HRID 656712 reaction equation
[Cl:1][C:2]1[C:3]([CH2:11][CH3:12])=[C:4]([NH2:10])[C:5]([CH2:8][CH3:9])=[CH:6][CH:7]=1.[N+:13]([O-])([OH:15])=[O:14]>OS(O)(=O)=O>[Cl:1][C:2]1[C:3]([CH2:11][CH3:12])=[C:4]([NH2:10])[C:5]([CH2:8][CH3:9])=[C:6]([N+:13]([O-:15])=[O:14])[CH:7]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 5978553-Chloro-2,6-diethylaniline

Product 1

HCID 59800724HCID 59800724, compoundYield 84.3%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

1.83 ml (10.9 mmol) 3-Chloro-2,6-diethyl-phenylamine (1) is dissolved on an ice-bath at 0° C. in 8 ml conc. H2SO4. 562 μl (12.0 mmol; 1.1 eq.) 90% ige HNO3 is added and the reaction mixture is stirred for 2.5 hours at 0° C. The reaction mixture is pored on ca. 200 ml ice and the obtained solution is extracted 8 times with 50 to 100 ml EE each. The combined organic layers are dried over magnesium sulphate and the solvent is removed under reduced pressure yielding 2.1 g of crude product. After purification by flash chromatography 1.24 g (5.42 mmol; 50%) of 2 could be obtained.

Workup

  1. extractionthe obtained solution is extracted 8 times with 50 to 100 ml EE each
  2. dry with materialThe combined organic layers are dried over magnesium sulphate
  3. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-af782a260a3d435c90bbedfac70ff201
Source dataset
uspto-grants-2011_12
Patent number
US08071810B2

Reaction notes

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