Diphenyl Ether → 8-Bromo-7-methoxy-1,6-naphthyridin-4(1H)-one

HRID 219146Notes

Reaction equation

HRID 219146 reaction equation
[Br:1][C:2]1[C:3]([O:20][CH3:21])=[N:4][CH:5]=[CH:6][C:7]=1[NH:8][CH:9]=[C:10]1[C:15](=[O:16])OC(C)(C)OC1=O.C1(OC2C=CC=CC=2)C=CC=CC=1>CCCCCC>[Br:1][C:2]1[C:3]([O:20][CH3:21])=[N:4][CH:5]=[C:6]2[C:7]=1[NH:8][CH:9]=[CH:10][C:15]2=[O:16]

Participants

4

Reactant 2

HCID 7583Diphenyl EtherHCID 673175935-[(3-Bromo-2-methoxy-pyridin-4-ylamino)-methylene]-2,2-dimethyl-[1,3]dioxane-4,6-dione

Product 1

HCID 673185318-Bromo-7-methoxy-1,6-naphthyridin-4(1H)-one

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent2×

Conditions

Temperature
250 °C

Procedure

A two neck round bottomed flask equipped with an air condenser was charged with 5-[(3-Bromo-2-methoxy-pyridin-4-ylamino)-methylene]-2,2-dimethyl-[1,3]dioxane-4,6-dione (23 g, 64 mmol) and diphenyl ether (230 mL) The reaction mixture was heated at 250° C. for 30 min under nitrogen atmosphere after which it was cooled to RT, diluted with hexane and filtered to obtain a dark solid. The crude product was refluxed in hexane for 30 min and filtered to obtained 8-Bromo-7-methoxy-1H-[1,6]naphthyridin-4-one as a brown solid.

Workup

  1. customA two neck round bottomed flask equipped with an air condenser
  2. temperaturewas cooled to RT
  3. filtrationfiltered
  4. customto obtain a dark solid
  5. filtrationfiltered

Sources & evidence

ORD record
ord-909fa4ffe37b4c8a8e7bd362b9a609e8
Source dataset
uspto-grants-2012_06
Patent number
US08198448B2

Reaction notes

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