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

HRID 2274195Notes

Reaction equation

HRID 2274195 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-0a3fef17e81b4e0c9dd9520146416fc9
Source dataset
uspto-grants-2015_09
Patent number
US09126951B2

Reaction notes

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