HCID 21543651, compound → HCID 15739388, compound

HRID 1606531Notes

Reaction equation

HRID 1606531 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]([NH:5][NH:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=1)=O>C1(O)C=CC=CC=1>[F:1][C:2]([F:18])([F:17])[C:3]1[N:8]2[C:9]3[C:14]([CH:15]=[CH:16][C:7]2=[N:6][N:5]=1)=[CH:13][CH:12]=[CH:11][CH:10]=3

Participants

3

Reactant 1

HCID 21543651HCID 21543651, compound

Product 1

HCID 15739388HCID 15739388, compound

Reagents, catalysts & solvents 1

HCID 996PhenolSolvent

Procedure

2-Hydrazinoquinoline (25.0 grams), 50 milliliters of trifluoroacetic acid, and 250 milliliters of xylene were combined in a 500-milliliter three-necked flask equipped with a condenser. The reaction mixture was refluxed overnight. In the morning it was allowed to cool and the solvent was stripped off, yielding 10 grams of a compound determined to be 2-(2-(trifluoroacetyl)hydrazino)quinoline. It was placed in 40 milliliters of phenol and refluxed for 20 hours. The reaction mixture was then steam distilled to remove the phenol, yielding the desired 1-trifluoromethyl-s-triazolo(4,3-a)quinoline product. It was recrystallized from ethanol, m.p., 133.5°-4.5°C.

Workup

  1. temperaturerefluxed for 20 hours
  2. distillationsteam distilled
  3. customto remove the phenol

Sources & evidence

ORD record
ord-088040d666e241fe94d68bdf64c40212
Source dataset
uspto-grants-1976_04
Patent number
US03953457

Reaction notes

Loading…