Carbon Dioxide → HCID 18372529, compound

HRID 323003Notes

Reaction equation

HRID 323003 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]([F:15])([F:14])[F:13])[CH:8]=[CH:7]2.[C:16]([O-])([O-:18])=[O:17].[K+].[K+].C(=O)=O>>[OH:1][C:2]1[C:3]([C:16]([OH:18])=[O:17])=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]([F:15])([F:13])[F:14])[CH:8]=[CH:7]2

Participants

4

Reactant 3

HCID 280Carbon DioxideHCID 11430Potassium CarbonateHCID 115720352-Trifluoromethylquinolin-8-ol

Product 1

HCID 18372529HCID 18372529, compoundYield 48.4%

Conditions

Temperature
170 °C

Procedure

8-Hydroxy-2-trifluoromethylquinoline (3.2 g) and K2CO3 (6.22 g) are placed in a stainless steel bomb. The bomb is pressurized slightly with CO2 and flushed 3×, then pressurized to approximately 800 psi CO2. The bomb is heated to 170° C., reaching a final pressure of approximately 1200 psi. This temperature and pressure are maintained for 7 days after which time the bomb is cooled and the pressure released. The solid residue is dissolved in a minimal amount of warm water. Any undissolved material is filtered and the aqueous filtrate is acidified to pH 4 with conc. HCl. The resulting tan solid is filtered and dried. The product is recrystallized with Et2O to give a light tan solid (1.87 g).

Workup

  1. customflushed 3×
  2. temperatureThis temperature and pressure are maintained for 7 days after which time the bomb
  3. temperatureis cooled
  4. dissolutionThe solid residue is dissolved in a minimal amount of warm water
  5. filtrationAny undissolved material is filtered
  6. filtrationThe resulting tan solid is filtered
  7. customdried
  8. customThe product is recrystallized with Et2O

Sources & evidence

ORD record
ord-5a39f1e13fbf415f90cd04438fae4022
Source dataset
uspto-grants-2001_04
Patent number
US06211376B1

Reaction notes

Loading…