Ammonia → HCID 20520021, compound

HRID 1076270Notes

Reaction equation

HRID 1076270 reaction equation
C([CH:3]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[C:6]([Cl:13])[N:5]=1)#N.[O-:20]C#N.[K+].OO.[Mn]([O-])(=O)(=O)=O.N>CC(C)=O.O>[C:3]([C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[C:6]([Cl:13])[N:5]=1)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

8

Reactant 5

HCID 222AmmoniaHCID 784Hydrogen PeroxideHCID 24401PermanganateHCID 11378442Potassium cyanateHCID 20520018HCID 20520018, compound

Product 1

HCID 20520021HCID 20520021, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Conditions

Temperature
15 °C

Procedure

Five hundred forty eight grams (2 moles) of 2-(cyanophenylmethyl)-3-nitro-6-chloropyridine were suspended in 3 liters of acetone and these were simultaneously dropped in at 37°C. a solution of 325 grams of potassium cyanate (4 moles) in 1 liter of water and a solution of 435 ml of 30% H2O2 (4.05 moles) in 800 ml of water. The reaction vessel was cooled with ice water. Both solutions were added within 45 minutes. After the end of the addition the color of the solution turned from the initial permanganate color (violet) solution to a light yellow. The solution was cooled in an ice bath to 15°C., then 600 grams of ice, 300 ml of 25% aqueous ammonia and 1 liter added with stirring. Yellow crystals separated out. They were filtered off with suction after 1 hour and washed with water. After boiling with 4 parts of methanol per part of crystals, cooling and filtering with suction there was obtained the pure 2-benzoyl-3-nitro-6-chloropyridine, M.P. 107°C.

Workup

  1. additionBoth solutions were added within 45 minutes
  2. additionAfter the end of the addition the color of the solution
  3. customYellow crystals separated out
  4. filtrationThey were filtered off with suction after 1 hour
  5. washwashed with water
  6. temperaturecooling
  7. filtrationfiltering with suction

Sources & evidence

ORD record
ord-7e60f04058e141638f36850b95b0697a
Source dataset
uspto-grants-1976_05
Patent number
US03956344

Reaction notes

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