2-((2-Chloro-4-nitrophenoxy)methyl)pyridine → 3-Chloro-4-(2-pyridylmethoxy)aniline

HRID 415014Notes

Reaction equation

HRID 415014 reaction equation
[Cl:1][C:2]1[CH:15]=[C:14]([N+:16]([O-])=O)[CH:13]=[CH:12][C:3]=1[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1>CO.[Pt]>[Cl:1][C:2]1[CH:15]=[C:14]([NH2:16])[CH:13]=[CH:12][C:3]=1[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1

Participants

4

Reactant 1

HCID 174694332-((2-Chloro-4-nitrophenoxy)methyl)pyridine

Product 1

HCID 167812123-Chloro-4-(2-pyridylmethoxy)anilineYield 80%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

2-(2-Chloro-4-nitro-phenoxymethyl)-pyridine (2.4 g, 9.07 mmol) is suspended in MeOH (30 ml) and treated wet 5% Pt/C (Degussa type, Aldrich, 0.8 g). The flask is flushed with hydrogen gas from a balloon and the reaction mixture is stirred under hydrogen atmosphere until reaction is complete by TLC (ca 2 hours). The reaction mixture is filtered through a Celite plug and the solvent is removed under reduced pressure. The crude product is redissolved in DCM, dried (MgSO4) and concentrated to yield 1.7 g (7.23 mmol, 80%) of the desired product.

Workup

  1. customThe flask is flushed with hydrogen gas from a balloon
  2. customis complete by TLC (ca 2 hours)
  3. filtrationThe reaction mixture is filtered through a Celite plug
  4. customthe solvent is removed under reduced pressure
  5. dissolutionThe crude product is redissolved in DCM
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-17e54a546047451089256049f10ba318
Source dataset
uspto-grants-2012_01
Patent number
US08088766B2

Reaction notes

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