Ammonium Chloride → N-(3-amino-5-(3-fluoropyridin-2-yl)phenyl)acetamide

HRID 64175Notes

Reaction equation

HRID 64175 reaction equation
[F:1][C:2]1[C:3]([C:8]2[CH:9]=[C:10]([NH:17][C:18](=[O:20])[CH3:19])[CH:11]=[C:12]([N+:14]([O-])=O)[CH:13]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.[NH4+].[Cl-]>C1COCC1.O.[Zn]>[NH2:14][C:12]1[CH:11]=[C:10]([NH:17][C:18](=[O:20])[CH3:19])[CH:9]=[C:8]([C:3]2[C:2]([F:1])=[CH:7][CH:6]=[CH:5][N:4]=2)[CH:13]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 89500321N-(3-(3-fluoropyridin-2-yl)-5-nitrophenyl)acetamide

Product 1

HCID 89500089N-(3-amino-5-(3-fluoropyridin-2-yl)phenyl)acetamideYield 90%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(3-(3-fluoropyridin-2-yl)-5-nitrophenyl)acetamide (5 g, 18.18 mmol) in THF (50 ml), Zn (11.8 g, 181.18 mmol) was added followed by slow addition of solution of NH4Cl (9.7 g, 181.18 mmol) in 20 ml water. The mixture was stirred at RT for 1 h. The mixture was filtered through celite and bed washed with ethyl acetate. The mixture was diluted with ethyl acetate and washed with water and brine solution, dried over sodium sulphate and distilled to give the product in 90% yield (4.2 g). LC-MS (ESI): Calculated mass: 245; Observed mass: 246.1 [M+H]+ (rt: 0.21 min).

Workup

  1. filtrationThe mixture was filtered through celite and bed
  2. washwashed with ethyl acetate
  3. additionThe mixture was diluted with ethyl acetate
  4. washwashed with water and brine solution
  5. dry with materialdried over sodium sulphate
  6. distillationdistilled
  7. customto give the product in 90% yield (4.2 g)
  8. custom246.1 [M+H]+ (rt: 0.21 min)

Sources & evidence

ORD record
ord-584e479d7680423386e4543843c4dfc0
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Reaction notes

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