Toluene → HCID 178517696, compound

HRID 1896502Notes

Reaction equation

HRID 1896502 reaction equation
[OH:1][C:2]1[CH:7]=[C:6](O)[CH:5]=[CH:4][N:3]=1.[F:9][C:10]([F:20])([F:19])[C:11]1[CH:12]=[C:13]([NH:17]N)[CH:14]=[CH:15][CH:16]=1.C1(C)C=CC=CC=1>C1(OC2C=CC=CC=2)C=CC=CC=1>[F:9][C:10]([F:19])([F:20])[C:11]1[CH:16]=[CH:15][C:14]2[C:7]3[C:2]([OH:1])=[N:3][CH:4]=[CH:5][C:6]=3[NH:17][C:13]=2[CH:12]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 98650(3-(Trifluoromethyl)phenyl)hydrazineHCID 178516518HCID 178516518, compound

Product 1

HCID 178517696HCID 178517696, compound

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Procedure

A mixture 2,4-dihydroxypyridine and 3-trifluoromethylphenylhydrazine (2.6 equiv) in diphenyl ether was heated at reflux with a Dean Stark apparatus for 2 h as described by C. H. Nguyen in Tetrahedron 1987, 43, 527. The reaction was cooled to room temperature followed by the addition of toluene. The solid was collected and washed with toluene. The solid was then dissolved in EtOAc and purified by flash chromatography (EtOAc to 5% MeOH in EtOAc) to provide the title compound.

Workup

  1. temperatureat reflux with a Dean Stark apparatus for 2 h
  2. customThe solid was collected
  3. washwashed with toluene
  4. dissolutionThe solid was then dissolved in EtOAc
  5. custompurified by flash chromatography (EtOAc to 5% MeOH in EtOAc)

Sources & evidence

ORD record
ord-7fba750c7ce946eb94357ff80d1ae41b
Source dataset
uspto-grants-2013_08
Patent number
US08518964B2

Reaction notes

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