HCID 178524738, compound → HCID 178516465, compound

HRID 1061740Notes

Reaction equation

HRID 1061740 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[N:7][C:8]([C:12]([F:15])([F:14])[F:13])=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1C(O)=O>C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1>[F:15][C:12]([F:13])([F:14])[C:8]1[N:7]=[C:6]2[C:11]([C:2]([OH:1])=[CH:3][CH:4]=[N:5]2)=[CH:10][CH:9]=1

Participants

3

Reactant 1

HCID 178524738HCID 178524738, compound

Product 1

HCID 178516465HCID 178516465, compound

Reagents, catalysts & solvents 1

HCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)Solvent

Procedure

4-Hydroxy-7-trifluoromethyl[1,8]-naphthyridine-3-carboxylic acid (14.0 g, 54.2 mmol) was added in portions to refluxing Dowtherm A (250 mL)—Care! Effervescence!—and the mixture was stirred at reflux for 80 min. The mixture was allowed to cool to room temperature, and a buff coloured solid precipitated from solution. The slurry was diluted with diethyl ether (250 mL) and the solid was separated by filtration, was washed with plenty of diethyl ether and was dried. This was 7-trifluoromethyl[1,8]naphthyridin-4-ol (11.6 g, 100%). δH (360 MHz, d6-DMSO) 6.15 (1H, d, J 7.4), 7.76 (1H, d, J 8.1), 8.06 (1H, d, J 7.4), 8.70 (1H, d, J 8.1). m/z (ES+) 215 [MH]+.

Workup

  1. temperatureat reflux for 80 min
  2. customprecipitated from solution
  3. additionThe slurry was diluted with diethyl ether (250 mL)
  4. customthe solid was separated by filtration
  5. washwas washed with plenty of diethyl ether
  6. customwas dried

Sources & evidence

ORD record
ord-b3fafbba64cd4770b5ca5ea88bc866db
Source dataset
uspto-grants-2005_11
Patent number
US06960598B2

Reaction notes

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