Hydrochloric Acid → 5-Fluoro-2,3-pyridinediamine

HRID 1386083Notes

Reaction equation

HRID 1386083 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([F:11])=[CH:4][N:3]=1.O.Cl>C(O)C.[Fe]>[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][C:5]([F:11])=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 217173395-Fluoro-3-nitropyridin-2-amine

Product 1

HCID 222931555-Fluoro-2,3-pyridinediamineYield 102.6%

Reagents, catalysts & solvents 2

HCID 23925IronCatalyst2×HCID 702EthanolSolvent

Procedure

To a solution of 2-amino-5-fluoro-3-nitropyridine (0.42 g, 2.3 mmol) and iron powder (1.6 g, 28 mmol) in ethanol (10 ml) were added water (0.5 ml, 28 mmol) and hydrochloric acid (27 μl, 0.32 mmol). The mixture was refluxed for 1 h. An additional amount of iron powder (0.2 g, 3.6 mmol) was added and the mixture was refluxed for 30 min. The reaction mixture was filtered through celite and evaporation under reduced pressure of the solvent gave 0.3 g (100%) of the desired product.

Workup

  1. temperatureThe mixture was refluxed for 1 h
  2. temperaturethe mixture was refluxed for 30 min
  3. filtrationThe reaction mixture was filtered through celite and evaporation under reduced pressure of the solvent

Sources & evidence

ORD record
ord-f899b9a40801482582da2ecd943dffa8
Source dataset
uspto-grants-2001_07
Patent number
US06265415B1

Reaction notes

Loading…