(2-Amino-6-methylpyridin-3-yl)methanol → 2-Amino-6-methylnicotinaldehyde

HRID 1891888Notes

Reaction equation

HRID 1891888 reaction equation
[NH2:1][C:2]1[C:7]([CH2:8][OH:9])=[CH:6][CH:5]=[C:4]([CH3:10])[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]([CH3:10])[N:3]=1

Participants

4

Reactant 1

HCID 55281422(2-Amino-6-methylpyridin-3-yl)methanol

Product 1

HCID 534010302-Amino-6-methylnicotinaldehydeYield 88%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a methylene chloride (8 mL) solution of (2-amino-6-methyl-pyridin-3-yl)-methanol (379 mg, 2.74 mmol) described in Manufacturing Example 170-1-3 was added manganese (IV) dioxide (1.19 mg, 13.7 mmol) at room temperature, which was stirred for 11 hours 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 (heptane:ethyl acetate=1:2) to obtain the title compound (328 mg, 88%).

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 (heptane:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-bb689ea10ca6461a90dc2a16efbfe184
Source dataset
uspto-grants-2013_08
Patent number
US08507530B2

Reaction notes

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