(S)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-2-nitropyridine → (S)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-2-aMine

HRID 1845894Notes

Reaction equation

HRID 1845894 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[C@@H:10]([O:12][C:13]1[C:14]([N+:19]([O-])=O)=[N:15][CH:16]=[CH:17][CH:18]=1)[CH3:11]>C(O)C.[Pd]>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[C@@H:10]([O:12][C:13]1[C:14]([NH2:19])=[N:15][CH:16]=[CH:17][CH:18]=1)[CH3:11]

Participants

4

Reactant 1

HCID 86327669(S)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-2-nitropyridine

Product 1

HCID 86327671(S)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-2-aMineYield 87%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The compound (S)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-2-nitropyridine (15.2 g, 45.9 mmol) was suspended in ethanol (150 mL), and palladium/carbon was added to perform the hydrogenation reaction. TLC test showed that the raw materials were completely reacted. The reaction liquid was filtered; the filtrate was concentrated under reduced pressure to remove ethanol to yield (S)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-2-aminopyridine (12 g, yield: 87%).

Workup

  1. customthe hydrogenation reaction
  2. customwere completely reacted
  3. customThe reaction liquid
  4. filtrationwas filtered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customto remove ethanol

Sources & evidence

ORD record
ord-5fe28263153a4bbc992eb0b5e618e4d9
Source dataset
uspto-grants-2015_02
Patent number
US08952002B2

Reaction notes

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