HCID 68089368, compound → HCID 86667815, compound

HRID 1615661Notes

Reaction equation

HRID 1615661 reaction equation
[N:1]1[C:2]([CH2:14][OH:15])=[N:3][N:4]2[C:13]=1[C:12]1[N:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH:6]=[CH:5]2>CCO.[O-2].[O-2].[Mn+4]>[N:1]1[C:2]([CH:14]=[O:15])=[N:3][N:4]2[C:13]=1[C:12]1[N:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH:6]=[CH:5]2

Participants

4

Reactant 1

HCID 68089368HCID 68089368, compound

Product 1

HCID 86667815HCID 86667815, compoundYield 100.9%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of [1,2,4]triazolo[1,5-h][1,7]naphthyridin-2-ylmethanol (280 mg, 1.4 mmol) in EtOH (20 mL) was added activated manganese (IV) dioxide (1.21 g, 14.0 mmol). The mixture was stirred at reflux for 2 h. Then the mixture was filtered and the filtrate was concentrated under reduce pressure to give [1,2,4]triazolo[1,5-h][1,7]naphthyridine-2-carbaldehyde as a yellow solid (280 mg, yield 88%). ESI MS: m/z 199.1 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 10.34 (s, 1H), 9.16 (dd, J=1.6, 4.4 Hz, 1H), 8.55 (d, J=7.2 Hz, 1H), 8.28 (dd, J=1.6, 8.0 Hz, 1H), 7.76 (dd, J=4.4, 8.0 Hz, 1H), 7.47 (d, J=8.8 Hz, 1H).

Workup

  1. temperatureat reflux for 2 h
  2. filtrationThen the mixture was filtered
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-efa18ecb484049ad906c90c34a9602da
Source dataset
uspto-grants-2014_07
Patent number
US08765760B2

Reaction notes

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