(3-Methoxymethoxypyridin-2-yl)-(4-nitrophenyl)methanol → 2-(4-Aminobenzyl)-3-methoxymethoxypyridine

HRID 2228186Notes

Reaction equation

HRID 2228186 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[C:6]([CH:11]([C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=2)O)=[N:7][CH:8]=[CH:9][CH:10]=1>C(O)C.[Pd]>[NH2:19][C:16]1[CH:15]=[CH:14][C:13]([CH2:11][C:6]2[C:5]([O:4][CH2:3][O:2][CH3:1])=[CH:10][CH:9]=[CH:8][N:7]=2)=[CH:18][CH:17]=1

Participants

4

Reactant 1

HCID 18472436(3-Methoxymethoxypyridin-2-yl)-(4-nitrophenyl)methanol

Product 1

HCID 184722062-(4-Aminobenzyl)-3-methoxymethoxypyridineYield 29.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of (3-methoxymethoxypyridin-2-yl)—(4-nitrophenyl)methanol (11.78 g) and 10% Pd-C (1.2 g) in ethanol (100 ml) was vigorously stirred under hydrogen atmosphere for 24 hours. The catalyst was filtered of, and the filtrate was concentrated under reduced pressure. The residue was separated and purified with column chromatography (ethyl acetate/hexane=1:1→2:1) to give 2—(4-aminobenzyl)-3-methoxymethoxypyridine (2.92 g) as orange oil.

Workup

  1. filtrationThe catalyst was filtered of, and the filtrate
  2. concentrationwas concentrated under reduced pressure
  3. customThe residue was separated
  4. custompurified with column chromatography (ethyl acetate/hexane=1:1→2:1)

Sources & evidence

ORD record
ord-0c578bfd9bb04612b4a50377a26f0a62
Source dataset
uspto-grants-2002_07
Patent number
US06413947B1

Reaction notes

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