Methyl 2-(hydroxymethyl)pyridine-4-carboxylate → Methyl 2-formylisonicotinate

HRID 2277541Notes

Reaction equation

HRID 2277541 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[C:7]([C:9]([O:11][CH3:12])=[O:10])[CH:6]=[CH:5][N:4]=1>C(Cl)Cl.O=[Mn]=O>[CH:2]([C:3]1[CH:8]=[C:7]([C:9]([O:11][CH3:12])=[O:10])[CH:6]=[CH:5][N:4]=1)=[O:1]

Participants

4

Reactant 1

HCID 13276248Methyl 2-(hydroxymethyl)pyridine-4-carboxylate

Product 1

HCID 19744506Methyl 2-formylisonicotinateYield 72%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 2-(hydroxymethyl)pyridine-4-carboxylate (30 g, 179.64 mmol) in DCM (1 L) was added MnO2 (93.77 g. 1.0778 mol) at r.t. and stirred overnight. The reaction mixture was then filtered and concentrated to afford the title compound (21.3 g, 72%). [M+H] Calc'd for C8H7NO3, 166. Found, 166.

Workup

  1. filtrationThe reaction mixture was then filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-6c865212858146c2b7ba0698c5b715d8
Source dataset
uspto-grants-2015_09
Patent number
US09133166B2

Reaction notes

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