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

HRID 1927253Notes

Reaction equation

HRID 1927253 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].ClCCl>[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 81.7%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of (2-amino-6-methoxymethyl-pyridin-3-yl)methanol (260 mg) described in Manufacturing Example 19-1 and dichloromethane (15 mL) was added manganese dioxide (1.3 g), which was stirred overnight at room temperature. The reaction mixture was filtered through Celite, and the filtrate was evaporated under a reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:heptane=3:2) to obtain the titled compound (210 mg).

Workup

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

Sources & evidence

ORD record
ord-0f1c38cb843043b2b863da99a2822f10
Source dataset
uspto-grants-2012_05
Patent number
US08183264B2

Reaction notes

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