Ammonium Chloride → 6-Iodopyridine-2,3-diamine

HRID 860047Notes

Reaction equation

HRID 860047 reaction equation
[I:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([N+:9]([O-])=O)=[CH:4][CH:3]=1.[NH4+].[Cl-]>[Fe].C(O)C.O>[I:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([NH2:9])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 23435516HCID 23435516, compound

Product 1

HCID 234354656-Iodopyridine-2,3-diamine

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Procedure

To a solution of 5-2 (2.0 g, 7.55 mmol) and NH4Cl (0.202 g, 3.78 mmol) in 2:1 EtOH-H2O (37.8 mL) at 90° C. was added iron powder (2.11 g, 37.8 mmol) in three equal portions over ten minutes. The reaction turned very dark in color. After sixty minutes the hot mixture was filtered through Celite then concentrated. The residue was partitioned between EtOAc and saturated NaHCO3 solution. The organic phase was washed with sat. NaHCO3 solution and brine, then dried with MgSO4 and concentrated to yield a brown solid.

Workup

  1. filtrationAfter sixty minutes the hot mixture was filtered through Celite
  2. concentrationthen concentrated
  3. customThe residue was partitioned between EtOAc and saturated NaHCO3 solution
  4. washThe organic phase was washed with sat. NaHCO3 solution and brine
  5. dry with materialdried with MgSO4
  6. concentrationconcentrated
  7. customto yield a brown solid

Sources & evidence

ORD record
ord-cd278b2148154362b480e11c81e379c0
Source dataset
uspto-grants-2006_12
Patent number
US07153862B2

Reaction notes

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