Diphenyl Ether → 6,7-Dimethoxy-1,5-naphthyridin-4-OL

HRID 1042871Notes

Reaction equation

HRID 1042871 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[N:11]=[CH:12]/[CH:13]2[C:18](=[O:19])OC(C)(C)OC2=O)[CH:6]=[N:7][C:8]=1[O:9][CH3:10].C1(OC2C=CC=CC=2)C=CC=CC=1>CCCCCC>[CH3:10][O:9][C:8]1[N:7]=[C:6]2[C:5](=[CH:4][C:3]=1[O:2][CH3:1])[NH:11][CH:12]=[CH:13][C:18]2=[O:19]

Participants

4

Reactant 2

HCID 7583Diphenyl EtherHCID 178493124HCID 178493124, compound

Product 1

HCID 673179326,7-Dimethoxy-1,5-naphthyridin-4-OL

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
200 °C

Procedure

A round bottom flask was charged with (E)-5-((5,6-dimethoxypyridin-3-ylimino)methyl)-2,2-dimethyl-1,3-dioxane-4,6-dione (450 mg, 1460 μmol) and 4.2 mL diphenyl ether. A reflux condenser was attached, and the solution was heated at 200° C. for 0.5 h. Upon cooling, hexane was added and the solids were filtered and washed with hexane. 6,7-dimethoxy-1,5-naphthyridin-4(1H)-one was isolated as a tan solid. MS [M+H]=207

Workup

  1. customA reflux condenser was attached
  2. temperatureUpon cooling
  3. filtrationthe solids were filtered
  4. washwashed with hexane

Sources & evidence

ORD record
ord-5382280c96c74f17b98dc573f7b927e5
Source dataset
uspto-grants-2013_10
Patent number
US08557816B2

Reaction notes

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