Ammonia → HCID 86718216, compound

HRID 1844189Notes

Reaction equation

HRID 1844189 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:11][CH2:12][C:13]2[C:18]([F:19])=[CH:17][CH:16]=[CH:15][N:14]=2)[C:5]([N+:8]([O-])=O)=[N:6][CH:7]=1.Cl.N>C(O)C.[Fe]>[Cl:1][C:2]1[CH:3]=[C:4]([O:11][CH2:12][C:13]2[C:18]([F:19])=[CH:17][CH:16]=[CH:15][N:14]=2)[C:5]([NH2:8])=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 86718217HCID 86718217, compound

Product 1

HCID 86718216HCID 86718216, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

Under argon, 29.8 g (105.1 mmol) of 5-chloro-3-[(3-fluoropyridin-2-yl)methoxy]-2-nitropyridine from Example 126A were initially charged in 317 ml of ethanol. 18.2 g (325.7 mmol) of iron powder were added, and the reaction mixture was heated to reflux. 80.4 ml of conc. hydrochloric acid were slowly added dropwise, and the mixture was heated under reflux for a further 6 h. The reaction mixture was made alkaline with 33% strength aqueous ammonia solution and then concentrated under reduced pressure. Purification by silica gel chromatography (mobile phase: dichloromethane/methanol gradient: 95/5 to 90/10) gave 25.0 g (94% of theory) of the target compound.

Workup

  1. temperaturethe reaction mixture was heated to reflux
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for a further 6 h
  4. concentrationconcentrated under reduced pressure
  5. customPurification by silica gel chromatography (mobile phase: dichloromethane/methanol gradient: 95/5 to 90/10)
  6. customgave 25.0 g (94% of theory) of the target compound

Sources & evidence

ORD record
ord-202177a9c4f74f9bbf53ac0ca22daf50
Source dataset
uspto-grants-2015_02
Patent number
US08946215B2

Reaction notes

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