Ammonia → 2-Chloro-4-nitroaminopyridine

HRID 2391747Notes

Reaction equation

HRID 2391747 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][N:3]=1.S(=O)(=O)(O)O.[N+:14]([O-])([OH:16])=[O:15].N>O>[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][N+:14]([O-:16])=[O:15])[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 844322-Chloropyridin-4-amine

Product 1

HCID 5814322-Chloro-4-nitroaminopyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

357.5 g of 2-chloropyridin-4-amine were added in portions to 2.28 l of cold concentrated sulfuric acid. 0.86 l of nitric acid (90%) were slowly added so that the temperature of the reaction mixture always stays below 10° C. After the addition the mixture was stirred for one hour at room temperature and poured into 4 l of water containing 10 kg of ice. 6.2125% (w/v) aqueous NH3 solution were slowly added. The resulting precipitate was filtered, washed with ice water and dried under vacuum to give 316.6 g of the 2-chloro-N-nitropyridin-4-amine. 316.2 g of this intermediate compound were treated with 2.35 l concentrated sulfuric acid and stirred for 30 minutes at 88-94° C. The mixture was cooled to room temperature and poured into 2 l of water containing 5 kg ice. 6.5 l 25% (w/v) aqueous NH3 solution were slowly added. The resulting precipitate was filtered and pre-dried under reduced pressure. Finally the residue was dried by azeotropic distillation with benzene. After crystallization from benzene the title compound was obtained.

Workup

  1. additionAfter the addition the mixture
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with ice water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-206495bfd76d459a86b0b6b5cea75bf4
Source dataset
uspto-grants-2012_09
Patent number
US08273890B2

Reaction notes

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