1,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene) → HCID 178516370, compound

HRID 81901

Reaction equation

HRID 81901 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N:8]=[CH:9][CH:10]2[C:15](=[O:16])OC(C)(C)OC2=O)[CH:5]=[N:6][CH:7]=1.C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1>>[Br:1][C:2]1[CH:3]=[C:4]2[C:5]([C:15]([OH:16])=[CH:10][CH:9]=[N:8]2)=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)HCID 575155695-{[(5-Bromopyridin-3-yl)imino]methyl}-2,2-dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 178516370HCID 178516370, compoundYield 76%

Conditions

Temperature
236.5 °C

Procedure

5-{[(5-Bromopyridin-3-yl)imino]methyl}-2,2-dimethyl-1,3-dioxane-4,6-dione (59 g, 0.18 mol) was slowly added to DOWTHERM A heat transfer fluid (2000 mL) over a period of 5 minutes at 235-238° C. Following addition, the reaction was maintained for an additional 5 minutes and then allowed to cool to 40° C. A brown precipitate formed, which was filtered and washed with hexanes (150 mL). The brown solid was suspended in an ethanol/water mixture (90:10, 1500 mL), heated to a boil for 30 minutes, isolated by filtration, and washed with ethanol (200 mL) to yield 30.8 g of 7-bromo[1,5]naphthyridin-4-ol as a dark brown powder.

Workup

  1. additionaddition
  2. temperaturethe reaction was maintained for an additional 5 minutes
  3. temperatureto cool to 40° C
  4. customA brown precipitate formed
  5. filtrationwhich was filtered
  6. washwashed with hexanes (150 mL)
  7. temperatureheated to a boil for 30 minutes
  8. customisolated by filtration
  9. washwashed with ethanol (200 mL)

Sources & evidence

ORD record
ord-df7ab2990c414418aed2ed5936119830
Source dataset
uspto-grants-2014_09
Patent number
US08846710B2

Linked notes

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