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

HRID 1930399Notes

Reaction equation

HRID 1930399 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)nicotinaldehydeYield 87.8%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
30 °C

Procedure

A mixture of (6-chloro-4-(methylamino)pyridin-3-yl)methanol (2.9 g, 16.7 mmol) and MnO2 (11.7 g, 133.6 mmol) in anhydrous DCM (25 mL) was stirred at 30° C. for 6 h. The reaction mixture was cooled to RT, and filtered. The filtrate was concentrated in vacuo to give 6-chloro-4-(methylamino)nicotinaldehyde (2.5 g, 87% yield). 1HNMR (400 MHz, DMSO-d6): δ 9.83 (s, 1 H), 8.52 (br s, 1 H), 8.40 (s, 1 H), 6.75 (s, 1 H), 2.87 (d, J=5.8 Hz, 3 H); MS (ESI) m/z: 171.0 [M+H]+.

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-9d37d64898964727b4bd88edb7542361
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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