HCID 67317382, compound → 6-(trifluoromethoxy)quinolin-4-ol

HRID 1013722Notes

Reaction equation

HRID 1013722 reaction equation
CC1(C)O[C:6](=[O:8])[C:5](=[CH:9][NH:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18]([F:21])([F:20])[F:19])=[CH:13][CH:12]=2)C(=O)O1>O(C1C=CC=CC=1)C1C=CC=CC=1.CCCCCC>[F:21][C:18]([F:19])([F:20])[O:17][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[NH:10][CH:9]=[CH:5][C:6]2=[O:8]

Participants

4

Reactant 1

HCID 67317382HCID 67317382, compound

Product 1

HCID 27751046-(trifluoromethoxy)quinolin-4-ol

Reagents, catalysts & solvents 2

HCID 7583Diphenyl EtherSolventHCID 8058HexaneSolvent

Conditions

Temperature
250 °C

Procedure

In a 50 mL round bottom flask with a reflux condenser attached was dissolved 2,2-dimethyl-5-((4-(trifluoromethoxy)phenylamino)methylene)-1,3-dioxane-4,6-dione (1.00 g, 3.02 mmol) in Ph2O (8.63 mL, 0.35 M). The mixture was heated to 250° C. in a heating mantle. At about 180° C., the reaction turned from a light yellow and homogeneous to an orange, then to a dark brown color and began to bubble, slowly at first and then more violently. Internal temperature of reaction went up to 230° C., although heating ceased at 180° C. Heating at 250° C. while stirring was continued for five minutes, and the reaction was cooled to RT, diluted with hexane, and the precipitate was filtered to yield 6-(trifluoromethoxy)quinolin-4(1H)-one as a crude brown solid. MS [M+H]=230.1; Calc'd 229.2 for C10H6F3NO2.

Workup

  1. customAt about 180° C.
  2. customto bubble
  3. customInternal temperature of reaction
  4. customwent up to 230° C.
  5. temperaturealthough heating
  6. customceased at 180° C
  7. temperatureHeating at 250° C.
  8. temperaturethe reaction was cooled to RT
  9. filtrationthe precipitate was filtered

Sources & evidence

ORD record
ord-8e3c64584d7c4987a9beb44241b2963c
Source dataset
uspto-grants-2011_07
Patent number
US07981891B2

Reaction notes

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