Ammonium Chloride → 2-Chloro-5-(4-methoxypyridin-2-yl)aniline

HRID 1059967Notes

Reaction equation

HRID 1059967 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[CH:10][N:9]=2)=[CH:4][C:3]=1[N+:16]([O-])=O.[Cl-].[NH4+]>C(O)C.O.[Fe]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[CH:10][N:9]=2)=[CH:4][C:3]=1[NH2:16]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 186675631-Chloro-4-(4-methoxypyridin-2-yl)-2-nitrobenzene

Product 1

HCID 186675322-Chloro-5-(4-methoxypyridin-2-yl)anilineYield 98.1%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a suspension of 1-chloro-4-(4-methoxypyridin-2-yl)-2-nitrobenzene (200 mg) in ethanol (6 ml) and water (0.6 ml) were added iron powder (206 mg) and ammonium chloride (28 mg), and the mixture was refluxed for 3 hours. The mixture was filtered, and the filtrate was evaporated under reduced pressure. To the residue were added ethyl acetate and water. The separated organic layer was washed with brine, dried over magnesium sulfate and evaporated under reduced pressure to give 2-chloro-5-(4-methoxypyridin-2-yl)aniline (174 mg).

Workup

  1. temperaturethe mixture was refluxed for 3 hours
  2. filtrationThe mixture was filtered
  3. customthe filtrate was evaporated under reduced pressure
  4. additionTo the residue were added ethyl acetate and water
  5. washThe separated organic layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-4504a36a778c4eb1963c155955dad364
Source dataset
uspto-grants-2003_02
Patent number
US06521643B1

Reaction notes

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