Imidazo[1,2-a]pyridine-7-methanol → Imidazo[1,2-A]pyridine-7-carbaldehyde

HRID 985534Notes

Reaction equation

HRID 985534 reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[CH:8][C:7]([CH2:10][OH:11])=[CH:6][C:5]=12>ClCCCl.[O-2].[Mn+4].[O-2]>[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[CH:8][C:7]([CH:10]=[O:11])=[CH:6][C:5]=12

Participants

4

Reactant 1

HCID 11051824Imidazo[1,2-a]pyridine-7-methanol

Product 1

HCID 11029972Imidazo[1,2-A]pyridine-7-carbaldehydeYield 69%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 111,2-DichloroethaneSolvent

Conditions

Temperature
50 °C

Procedure

Imidazo[1,2-α]pyridin-7-ylmethanol (1.35 g, 9.38 mmol) was suspended in 1,2-dichloroethane (40 ml), manganese(IV) oxide (4.07 g, 46.9 mmol) added and the mixture heated at 50° C. for 16 h. The mixture was cooled to ambient temperature, filtered through Celite® and evaporated to dryness to give imidazo[1,2-α]pyridine-7-carboxaldehyde (0.92 g, 69%) as a yellow solid. 1H NMR (400 MHz, CDCl3) δH 7.34 (1H, dd, J 7 and 1), 7.75 (1H, s), 7.87 (1H, s), 8.13 (1H, s), 8.21 (1H, d, J 7), 10.00 (1H, s).

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. filtrationfiltered through Celite®
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-05dc5a6338e4474ba606d3fb4495e89e
Source dataset
uspto-grants-2005_03
Patent number
US06872731B2

Reaction notes

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