Ammonia → 6-Chloro-3-nitropyridin-2-ylamine

HRID 25863

Reaction equation

HRID 25863 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[N:3]=1.CCO.O.[NH3:16]>>[Cl:11][C:4]1[N:3]=[C:2]([NH2:16])[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=1

Participants

5

Reactant 4

HCID 222AmmoniaHCID 702EthanolHCID 962WaterHCID 852392,6-Dichloro-3-nitropyridine

Product 1

HCID 27240356-Chloro-3-nitropyridin-2-ylamineYield 89%

Procedure

2,6-Dichloro-3-nitropyridine 90 (10.0 g, 51.8 mmol) was dissolved in 37 ml of a 7N solution of NH3 in EtOH (0.26 mol, 5.0 eqv) and the solution was stirred at rt for 24 h. H2O (40 ml) was added and the resulting mixture was filtered to collect the crude yellow product. The solid material was dissolved in CH2Cl2 and then extracted with a 1N HCl solution. The aqueous extracts were combined and then neutralized with NaHCO3 before being re-extracted with CH2Cl2. The organic fractions were combined, dried (MgSO4), filtered, and concentrated in vacuo to yield 8.0 g of a yellow solid (89%): 1H NMR (400 MHz, d6-DMSO) d 6.77 (d, J=8.8 Hz, 1H), 8.27 (s, 2H), 8.39 (d, J=8.4 Hz, 1H); 13C NMR (125 MHz, d6-DMSO) d 111.89, 126.02, 138.28, 153.36, 154.88; HRMS (EI) Calcd for C5H4ClN3O2: 172.9997. Found 172.9996.

Workup

  1. filtrationthe resulting mixture was filtered
  2. customto collect the crude yellow product
  3. dissolutionThe solid material was dissolved in CH2Cl2
  4. extractionextracted with a 1N HCl solution
  5. extractionbefore being re-extracted with CH2Cl2
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c508e66893ef4c08bd21193572dff79f
Source dataset
uspto-grants-2005_02
Patent number
US06858600B2

Linked notes

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