(2-Amino-6-methoxymethyl-pyridin-3-yl)methanol → 2-Amino-6-methoxymethyl-pyridine-3-carbaldehyde

HRID 640131Notes

Reaction equation

HRID 640131 reaction equation
[NH2:1][C:2]1[C:7]([CH2:8][OH:9])=[CH:6][CH:5]=[C:4]([CH2:10][O:11][CH3:12])[N:3]=1>[O-2].[O-2].[Mn+4].C(Cl)Cl>[NH2:1][C:2]1[C:7]([CH:8]=[O:9])=[CH:6][CH:5]=[C:4]([CH2:10][O:11][CH3:12])[N:3]=1

Participants

4

Reactant 1

HCID 59255403(2-Amino-6-methoxymethyl-pyridin-3-yl)methanol

Product 1

HCID 592554632-Amino-6-methoxymethyl-pyridine-3-carbaldehydeYield 84.2%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of (2-amino-6-methoxymethyl-pyridin-3-yl)methanol (260 mg, 1.5 mmol) described in Manufacturing Example 26-1-5 and methylene chloride (15 mL) was added manganese dioxide (1.3 g, 15 mmol), which was stirred overnight at room temperature. The reaction mixture was filtered through a Celite pad, and the filtrate was concentrated under a reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:heptane=3:2) to obtain the title compound (210 mg, 81%).

Workup

  1. filtrationThe reaction mixture was filtered through a Celite pad
  2. concentrationthe filtrate was concentrated under a reduced pressure
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate:heptane=3:2)

Sources & evidence

ORD record
ord-a748a496872b48b7932cf2d1f5f8a024
Source dataset
uspto-grants-2010_04
Patent number
US07691882B2

Reaction notes

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