Ammonium Chloride → 2,6-Dichloro-3-pyridylamine

HRID 2210423Notes

Reaction equation

HRID 2210423 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[C:4]([Cl:11])[N:3]=1.[NH4+].[Cl-]>CO.CC(C)=O>[NH2:8][C:7]1[C:2]([Cl:1])=[N:3][C:4]([Cl:11])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 25517Ammonium ChlorideHCID 852392,6-Dichloro-3-nitropyridine

Product 1

HCID 1128462,6-Dichloro-3-pyridylamine

Reagents, catalysts & solvents 1

HCID 21894497Aceton-methanolSolvent

Procedure

4 g of 2,6-dichloro-3-nitropyridine are added to a suspension of 8 g of reduced iron in 200 cm3 of a water/alcohol (50/50) solution containing 1.6 g of NH4Cl. The suspension is brought to reflux for 1 hour. The insoluble material is then removed by filtration. The filtrate is treated with 0.4 g of Na2SO3 and 0.4 g of NaH2PO2. The solution is adjusted to a pH of 8 and the alcohol is concentrated under reduced pressure until precipitation. The crystals corresponding to 3-amino-2,6- dichloropyridine are collected on a filter, washed with water and dried.

Workup

  1. temperatureto reflux for 1 hour
  2. customThe insoluble material is then removed by filtration
  3. additionThe filtrate is treated with 0.4 g of Na2SO3 and 0.4 g of NaH2PO2
  4. concentrationthe alcohol is concentrated under reduced pressure until precipitation
  5. customThe crystals corresponding to 3-amino-2,6- dichloropyridine are collected on a filter
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-f865142e0abc458f8cdf751471a28166
Source dataset
uspto-grants-1995_10
Patent number
US05459138

Reaction notes

Loading…