Ammonium formate → HCID 22592496, compound

HRID 22906Notes

Reaction equation

HRID 22906 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N+:10]([O-])=O)[CH:5]=[CH:6][C:7]=1[S:8][CH3:9].C([O-])=O.[NH4+]>C1COCC1.CO.C(OCC)(=O)C.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([NH2:10])[CH:5]=[CH:6][C:7]=1[S:8][CH3:9]

Participants

6

Reactant 2

HCID 2723923Ammonium formate2×HCID 225925052-Fluoro-4-nitrothioanisole

Product 1

HCID 22592496HCID 22592496, compoundYield 88%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

10.0 g of 3-fluoro-4-methylsulfanylnitrobenzene prepared in the above example 1, 0.1 eq of Pd/C (5 wt %), 4 eq of amonium formate were dissolved in THF/MeOH (1:1) and refluxed for 3 hours. The solid, which was not dissolved in the solution, was filtered away, and the filtrate was distilled under reduced pressure to obtain oily compound, which was dissolved again in 80 ml of ethyl acetate. Solid amonium formate which was not dissolved in the solution, was filtered away, and the filtrate was distilled under reduced pressure to obtain oily filtrate, which was purified by column chromatography (ethyl acetate:n-Hexane=1:3) to give 6.04 g of the title compound as a yellow solid (yield 88%).

Workup

  1. temperaturerefluxed for 3 hours
  2. dissolutionThe solid, which was not dissolved in the solution
  3. filtrationwas filtered away
  4. distillationthe filtrate was distilled under reduced pressure
  5. customto obtain oily compound, which
  6. filtrationwas filtered away
  7. distillationthe filtrate was distilled under reduced pressure
  8. customto obtain oily filtrate, which
  9. customwas purified by column chromatography (ethyl acetate:n-Hexane=1:3)

Sources & evidence

ORD record
ord-fc9fc956e2f544e2a1d6fb3d8bcc198d
Source dataset
uspto-grants-2005_02
Patent number
US06849652B1

Reaction notes

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