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

HRID 1277171Notes

Reaction equation

HRID 1277171 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-b6027d1831e14029a090d80b2d8d510a
Source dataset
uspto-grants-2000_12
Patent number
US06166006

Reaction notes

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