Nitric Acid → HCID 178526657, compound

HRID 327765Notes

Reaction equation

HRID 327765 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5](N)=[N:6][CH:7]=1.S(=O)(=O)(O)O.[N:14]([O-:16])=[O:15].[Na+].[N+]([O-])(O)=[O:19]>O>[Cl:1][C:2]1[CH:3]=[C:4]([N+:14]([O-:16])=[O:15])[C:5]([OH:19])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 661742-Amino-5-chloropyridineHCID 23668193Sodium Nitrite

Product 1

HCID 178526657HCID 178526657, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

321 g of 5-chloro-2-aminopyridine are added dropwise to 1.25 l of concentrated sulfuric acid. The reaction mixture is then stirred until the educt has completely dissolved. Then 172.5 g of sodium nitrite, dissolved in 240 ml of water, are added at a temperature of 40°-45° C. and the reaction mixture is stirred for 15 minutes. Subsequently 125 ml of 100% nitric acid are added dropwise at 50° C. over 40 minutes. The reaction mixture is kept for 1 hour at 55° C. and then poured onto 5 kg of ice-water. The product in the form of a yellow precipitate is isolated by filtration, washed copiously with water and subsequently dried at 60° C., giving 351 g of 5-chloro-2-hydroxy-3-nitropyridine (80.5% of theory) with a melting point of 229°-231° C.

Workup

  1. dissolutionhas completely dissolved
  2. additionare added at a temperature of 40°-45° C.
  3. stirringthe reaction mixture is stirred for 15 minutes
  4. customThe product in the form of a yellow precipitate is isolated by filtration
  5. washwashed copiously with water
  6. customsubsequently dried at 60° C.

Sources & evidence

ORD record
ord-47754fd775de4f5dbaa7fd42c1bba3e5
Source dataset
uspto-grants-1993_12
Patent number
US05274100

Reaction notes

Loading…