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

HRID 710576Notes

Reaction equation

HRID 710576 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>C(Cl)Cl.O=[Mn]=O>[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

4

Reactant 1

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

Product 1

HCID 234345716-Chloro-4-(methylamino)nicotinaldehyde

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

(6-Chloro-4-(methylamino)pyridin-3-yl)methanol (20 g, 116 mmol) was dissolved in DCM (250 mL) and MnO2 (100 g, 1.16 mol) was added. The reaction mixture was stirred at rt overnight, then filtered through a celite plug and washed with ethyl acetate. The filtrate was concentrated to obtain the title compound. 1H NMR (300 MHz, CDCl3) δ 9.85 (s, 1H), 8.59 (bs, 1H), 8.31 (s, 1H), 6.59 (s, 1H), 2.96 (d, J=5.1 Hz, 3H).

Workup

  1. filtrationfiltered through a celite plug
  2. washwashed with ethyl acetate
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-f439c944e9f14efb8907fab138058f50
Source dataset
uspto-grants-2015_11
Patent number
US09181238B2

Reaction notes

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