Diethyl Ether → HCID 178463016, compound

HRID 542564Notes

Reaction equation

HRID 542564 reaction equation
[CH2:1]([N:3]1[C:7]2=[N:8][CH:9]=C[C:11]([CH:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=3)O)([O:12]N=C(C)C)[C:6]2=[CH:5][NH:4]1)[CH3:2].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.CCOCC>ClCCl>[CH2:1]([N:3]1[C:7]2=[N:8][CH:9]=[C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=3)[C:11]([OH:12])=[C:6]2[CH:5]=[N:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 178418287HCID 178418287, compoundHCID 178462993HCID 178462993, compound

Product 1

HCID 178463016HCID 178463016, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(1-Ethyl-4-isopropylideneaminooxy-1H-pyrazolo[3,4-b]pyridine-4-yl) (2-pyridyl)carbinol (8.3 g) was dissolved in 150 ml of dichloromethane and to this was added 6.5 g of pyridinium chlorochromate. The reaction mixture was stirred 1 hour and then 300 ml of ether was added, after which the mixture was filtered through a pad of magnesium silicate. The pad was washed with a total of 2 liters of ether and then with 1 liter of 5% methanol/dichloromethane. Concentration of the combined filtrate under a reduced pressure gave 5.8 g of the 1-ethyl-4-hydroxy-5-(2-pyridinyl)-1H-pyrazolo[3,4-b]pyridine, whose identity was confirmed by its mass spectrum.

Workup

  1. filtrationafter which the mixture was filtered through a pad of magnesium silicate
  2. washThe pad was washed with a total of 2 liters of ether

Sources & evidence

ORD record
ord-dfaedddb1d26455d9b8c56d895894252
Source dataset
uspto-grants-1987_04
Patent number
US04658029

Reaction notes

Loading…