1,4-Dioxane → 8-Hydroxy-quinazoline-2-carboxaldehyde

HRID 640784Notes

Reaction equation

HRID 640784 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH3:12])[N:8]=[CH:7]2.[O:13]1CCOCC1>>[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH:12]=[O:13])[N:8]=[CH:7]2

Participants

3

Reactant 2

HCID 312751,4-Dioxane2×HCID 106070502-Methylquinazolin-8-ol

Product 1

HCID 592565308-Hydroxy-quinazoline-2-carboxaldehyde

Conditions

Temperature
80 °C

Procedure

A solution of 8-hydroxy-2-methyl-quinazoline (A3) (5 mmol) in dioxane (10 mL) was added dropwise over 3 h into a stirred mixture of SeO2 (8.8 mmol) in dioxane (30 mL) at 50° C. The resulting mixture was then heated at 80° C. for 16 h, allowed to cool, and the solids filtered off. The filtrate was concentrated and purified via column chromatography on silica (dichloromethane/MeOH, 40:1). This afforded 8-hydroxy-quinazoline-2-carboxaldehyde (2) as a solid.

Workup

  1. temperatureto cool
  2. filtrationthe solids filtered off
  3. concentrationThe filtrate was concentrated
  4. custompurified via column chromatography on silica (dichloromethane/MeOH, 40:1)

Sources & evidence

ORD record
ord-d8572207320843eabcd083b04b20af2d
Source dataset
uspto-grants-2010_04
Patent number
US07692011B2

Reaction notes

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