Potassium Carbonate → HCID 178524138, compound

HRID 323004Notes

Reaction equation

HRID 323004 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:12]=[C:11]([OH:13])[C:10]2[C:5](=[C:6]([OH:14])[CH:7]=[CH:8][CH:9]=2)[N:4]=1.[C:17]([O-])([O-:19])=[O:18].[K+].[K+]>>[OH:13][C:11]1[C:10]2[C:5](=[C:6]([OH:14])[C:7]([C:17]([OH:19])=[O:18])=[CH:8][CH:9]=2)[N:4]=[C:3]([C:2]([F:1])([F:15])[F:16])[CH:12]=1

Participants

3

Reactant 2

HCID 11430Potassium CarbonateHCID 178516138HCID 178516138, compound

Product 1

HCID 178524138HCID 178524138, compound

Conditions

Temperature
170 °C

Procedure

2-Trifluoromethyl-4,8-dihydroxyquinoline (6.0 g) and K2CO3 (11.0 g) are mixed in a stainless steel bomb. The bomb is flushed and evacuated 3× with 100 psi CO2. The reaction vessel is then pressurized to 800 psi CO2 and heated to 170° C., reaching a final pressure of 1200 psi. The bomb remains at this temperature and pressure for 7 days. The reaction vessel is cooled to room temperature, the pressure is released, and the reaction mixture is dissolved in 300 mL hot water. Any undissolved material is filtered and the filtrate is acidified with conc. HCl. A precipitate at pH 7 is collected (starting material). The filtrate is further acidified to pH 4 where a tan solid is collected (starting material+desired product). Since most of the solid collected is starting material, this material is reacted in the bomb for 7 more days. The same workup as before is done, with the only precipitate collected at pH 4.5. The desired product is filtered, dried, and recrystallized very slowly with EtOAc/hexanes (0.41 g).

Workup

  1. customThe bomb is flushed
  2. customevacuated 3× with 100 psi CO2
  3. temperatureThe reaction vessel is cooled to room temperature
  4. dissolutionthe reaction mixture is dissolved in 300 mL hot water
  5. filtrationAny undissolved material is filtered
  6. customA precipitate at pH 7 is collected (starting material)
  7. customis collected (starting material+desired product)
  8. customSince most of the solid collected
  9. customthis material is reacted in the bomb for 7 more days
  10. customcollected at pH 4.5
  11. filtrationThe desired product is filtered
  12. customdried
  13. customrecrystallized very slowly with EtOAc/hexanes (0.41 g)

Sources & evidence

ORD record
ord-77806c1d727e4b1c8f3ede0bc781129d
Source dataset
uspto-grants-2001_04
Patent number
US06211376B1

Reaction notes

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