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

HRID 524051Notes

Reaction equation

HRID 524051 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-91f62f4b2cc8480080b516bf35366868
Source dataset
uspto-grants-2016_05
Patent number
US09340514B2

Reaction notes

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