2-[(2-Chloro-4-nitrophenoxy)methyl]-6-methylpyridine → 3-Chloro-4-[(6-methylpyridin-2-yl)methoxy]aniline

HRID 877088Notes

Reaction equation

HRID 877088 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:17]([O-])=O)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[N:11]=1>CO.[Pt]>[Cl:1][C:2]1[CH:3]=[C:4]([NH2:17])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[N:11]=1

Participants

4

Reactant 1

HCID 668773902-[(2-Chloro-4-nitrophenoxy)methyl]-6-methylpyridine

Product 1

HCID 220552383-Chloro-4-[(6-methylpyridin-2-yl)methoxy]anilineYield 88.5%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

2.79 g of compound 9.1 (10 mmol) was suspended in MeOH (50 ml) and treated wet 5% Pt/C (Degussa type, Aldrich, 1.5 g). The flask is flushed with hydrogen gas from a balloon and the reaction mixture was stirred under hydrogen balloon for 2 hours. The reaction mixture was filtered through a Celite plug and the solvent is removed under reduced pressure to yield 2.2 g of the desired product.

Workup

  1. customThe flask is flushed with hydrogen gas from a balloon
  2. filtrationThe reaction mixture was filtered through a Celite plug
  3. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-0465f44a828b4cd886c20b9737205fb0
Source dataset
uspto-grants-2015_03
Patent number
US08987284B2

Reaction notes

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