(6-Chloro-4-(methylamino)pyridin-3-yl)methanol → 6-Chloro-4-(methylamino)nicotinaldehyde

HRID 2404034Notes

Reaction equation

HRID 2404034 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][OH:9])=[C:4]([NH:10][CH3:11])[CH:3]=1>ClCCl.C1COCC1.[O-2].[Mn+4].[O-2]>[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][CH3:11])[C:5]([CH:8]=[O:9])=[CH:6][N:7]=1

Participants

5

Reactant 1

HCID 51000240(6-Chloro-4-(methylamino)pyridin-3-yl)methanol

Product 1

HCID 234345716-Chloro-4-(methylamino)nicotinaldehydeYield 87.8%

Reagents, catalysts & solvents 3

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (6-chloro-4-(methylamino)pyridin-3-yl)methanol (4.2 g, 24.7 mmol) and manganese(IV) oxide (active, 25.8 g, 296.6 mmol) in dichloromethane (50 mL) and THF (50 mL) was stirred at RT overnight. LCMS showed the reaction was completed. The solid was filtered off, and the filtrate was concentrated to afford the title compound (3.7 g, crude) as a light yellow solid, which was directly used in the next step without further purification. MS (ES+) C7H7ClN2O requires: 170, 172. found: 171, 173 [M+H]+.

Workup

  1. filtrationThe solid was filtered off
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-12b7f96e5dea4bf38367a49cedeead48
Source dataset
uspto-grants-2014_08
Patent number
US08802697B2

Reaction notes

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