(6-Chloro-4-(phenylamino)pyridin-3-yl)methanol → 6-Chloro-4-phenylamino-pyridine-3-carbaldehyde

HRID 1930299Notes

Reaction equation

HRID 1930299 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][OH:9])=[C:4]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:3]=1>C(Cl)Cl.O=[Mn]=O>[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:5]([CH:8]=[O:9])=[CH:6][N:7]=1

Participants

4

Reactant 1

HCID 86620159(6-Chloro-4-(phenylamino)pyridin-3-yl)methanol

Product 1

HCID 592123486-Chloro-4-phenylamino-pyridine-3-carbaldehydeYield 86%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

MnO2 (39 g, 448 mmol) was added to a solution of (6-chloro-4-phenylamino-pyridin-3-yl)-methanol (13 g, 56 mmol) in CH2Cl2 (100 ml) and the mixture was stirred at RT overnight. The solids was removed by filtration and the filtrate was concentrated to give 6-chloro-4-(phenylamino)nicotinaldehyde (11 g, 86% yield). 1H-NMR (400 MHz, DMSO-d6): δ 10.18 (s, 1H), 9.99 (s, 1 H), 8.62 (s, 1 H), 7.49-7.31 (m, 5 H), 6.80 (s, 1 H).

Workup

  1. customThe solids was removed by filtration
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-ebf072c8500f416f8157b4968a82ffd2
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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