5-Nitro-2-(2,2,3,3-tetrafluoro-propoxy)pyridine → 6-(2,2,3,3-Tetrafluoropropoxy)pyridin-3-amine

HRID 450086Notes

Reaction equation

HRID 450086 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:10][CH2:11][C:12]([F:17])([F:16])[CH:13]([F:15])[F:14])=[N:8][CH:9]=1)([O-])=O>CO.[Pd]>[F:17][C:12]([F:16])([CH:13]([F:15])[F:14])[CH2:11][O:10][C:7]1[N:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 866211495-Nitro-2-(2,2,3,3-tetrafluoro-propoxy)pyridine

Product 1

HCID 290042936-(2,2,3,3-Tetrafluoropropoxy)pyridin-3-amineYield 446.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 5-nitro-2-(2,2,3,3-tetrafluoro-propoxy)pyridine (1.5 g, 0.6 mmol) in methanol (30 ml) was hydrogenated over 10% Pd—C (150 mg) at atmospheric pressure until no further gas was absorbed. The reaction mixture was filtered over celite and the filtrate concentrated to dryness to yield 6-(2,2,3,3-tetrafluoro propoxy)-pyridin-3-ylamine (600 mg, 50%) as solid.

Workup

  1. customwas absorbed
  2. filtrationThe reaction mixture was filtered over celite
  3. concentrationthe filtrate concentrated to dryness

Sources & evidence

ORD record
ord-490fbc9cb9c140babc116dfc025f2c09
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Reaction notes

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