(6-Chloro-5-methyl-4-(methylamino)pyridin-3-yl)methanol → 6-Chloro-5-methyl-4-(methylamino)nicotinaldehyde

HRID 2274210Notes

Reaction equation

HRID 2274210 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][OH:9])=[C:4]([NH:10][CH3:11])[C:3]=1[CH3:12]>ClCCl.[O-2].[Mn+2]>[Cl:1][C:2]1[C:3]([CH3:12])=[C:4]([NH:10][CH3:11])[C:5]([CH:8]=[O:9])=[CH:6][N:7]=1

Participants

4

Reactant 1

HCID 86713589(6-Chloro-5-methyl-4-(methylamino)pyridin-3-yl)methanol

Product 1

HCID 867135906-Chloro-5-methyl-4-(methylamino)nicotinaldehydeYield 81.2%

Reagents, catalysts & solvents 2

HCID 160959Manganese oxideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of (6-chloro-5-methyl-4-(methylamino)pyridin-3-yl)methanol (1.4 g, 8.0 mmol) and manganese oxide (2.8 g, 32 mmol) in dichloromethane (100 mL) was stirred at RT for 4 h. LCMS monitored the reaction was completed. The solid was filtered off, and the filtrate was concentrated to get the title compound (1.2 g, crude) as a yellow oil. MS (ES+) C8H9ClN2O requires: 184, 186. Found: 185, 187 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-e0ae1a4c8a5c43929feead221b402c99
Source dataset
uspto-grants-2015_09
Patent number
US09126951B2

Reaction notes

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