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

HRID 1257173Notes

Reaction equation

HRID 1257173 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) and 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 9.82 (s, 1H), 8.51 (br s, 1H), 8.27 (s, 1H), 6.56 (s, 1H), 3.28 (m, 2H), 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-776f3617a70f4fc4b334523adabde59d
Source dataset
uspto-grants-2013_06
Patent number
US08461179B1

Reaction notes

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