Ammonium formate → 3-[(E)-2-(3-aminophenyl)vinyl]-5-bromopyridine

HRID 1953404Notes

Reaction equation

HRID 1953404 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6](/[CH:8]=[CH:9]/[C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-])=O)[CH:11]=2)[CH:7]=1.C([O-])=O.[NH4+]>C(O)C.O.[Fe]>[NH2:16][C:12]1[CH:11]=[C:10](/[CH:9]=[CH:8]/[C:6]2[CH:5]=[N:4][CH:3]=[C:2]([Br:1])[CH:7]=2)[CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 232981253-bromo-5-[(E)-2-(3-nitrophenyl)vinyl]pyridine

Product 1

HCID 232980903-[(E)-2-(3-aminophenyl)vinyl]-5-bromopyridineYield 71.3%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 3-bromo-5-[(E)-2-(3-nitrophenyl)vinyl]pyridine (5.55 g), iron powder (3.05 g) and ammonium formate (5.73 g) in ethanol (90 ml) and water (30 ml) was stirred at 90pbC. for 30 minutes. The mixture was filtered while hot. The filtrate was added to sodium bicarbonate solution and extracted with ethyl acetate twice. The combined organic solution was washed with sodium bicarbonate solution and brine, dried over magnesium sulfate and concentrated to give 3-[(E)-2-(3-aminophenyl)vinyl]-5-bromopyridine (3.57 g).

Workup

  1. filtrationThe mixture was filtered while hot
  2. additionThe filtrate was added to sodium bicarbonate solution
  3. extractionextracted with ethyl acetate twice
  4. washThe combined organic solution was washed with sodium bicarbonate solution and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-42dfc52151bd4790bacaafcbd35d61f8
Source dataset
uspto-grants-2000_09
Patent number
US06117875

Reaction notes

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