HCID 58009138, compound → 6-Chloro-4-(ethylamino)-3-pyridinecarboxaldehyde

HRID 1930403Notes

Reaction equation

HRID 1930403 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][OH:9])=[C:4]([NH:10][CH2:11][CH3:12])[CH:3]=1>C(Cl)Cl.O=[Mn]=O>[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][CH2:11][CH3:12])[C:5]([CH:8]=[O:9])=[CH:6][N:7]=1

Participants

4

Reactant 1

HCID 58009138HCID 58009138, compound

Product 1

HCID 552964106-Chloro-4-(ethylamino)-3-pyridinecarboxaldehydeYield 89%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (6-chloro-4-(ethylamino)pyridin-3-yl)methanol (2.5 g, 13.4 mmol) in DCM (30 mL) was added MnO2 (5.8 g, 67 mmol), then the reaction mixture was stirred at RT overnight. The reaction mixture was filtered and the filtrate was concentrated in vacuo to give 6-chloro-4-(ethylamino)nicotinaldehyde (2.2 g, 89% yield). 1H-NMR (400 MHz, CDCl3): δ δ 9.82 (s, 1 H), 8.51 (br s, 1 H), 8.27 (s, 1 H), 6.56 (s, 1 H), 3.28 (m, 2 H), 1.31 (t, J=7.2 Hz, 3H); MS (ESI) m/z: 185.0 [M+H]+.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-fc5951fa930c4e2096749047e14977bb
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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