Dibromomethane → HCID 20290824, compound

HRID 1413818Notes

Reaction equation

HRID 1413818 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:14]([OH:23])([C:19]([F:22])([F:21])[F:20])[C:15]([F:18])([F:17])[F:16])[CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[CH:8]=[C:7]2[CH3:13].[C:24](=O)([O-])[O-].[K+].[K+].BrCBr>O>[CH3:13][C:7]1[C:6]2[C:11]3=[C:2]([O:1][CH2:24][N:10]3[C:9](=[O:12])[CH:8]=1)[CH:3]=[C:4]([C:14]([OH:23])([C:19]([F:22])([F:20])[F:21])[C:15]([F:16])([F:17])[F:18])[CH:5]=2

Participants

5

Reactant 3

HCID 3024DibromomethaneHCID 11430Potassium CarbonateHCID 20290835HCID 20290835, compound

Product 1

HCID 20290824HCID 20290824, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 6.8 gm. (0.02 mole) of 8-hydroxy-4-methyl-6-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]-2(1H)-quinolinone is added 2.8 gm. (0.02 mole) of potassium carbonate and 25.3 gm. (0.15 mole) of dibromomethane. The solution is heated and stirred at 70° in a nitrogen atmosphere for 4 hours. At the end of this period the solution is cooled and added to 50 ml. of water. The resultant solid is filtered and purified by chromatography on silicic acid. Elution with 97.5% chloroform/2.5% methanol gives 2.0 gm. of 6-methyl-8-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]-2H,4H-oxazolo[5,4,3-ij]quinolin-4-one, recrystallized from acetonitrile, m.p. 262°-264°.

Workup

  1. temperatureThe solution is heated
  2. temperatureAt the end of this period the solution is cooled
  3. additionadded to 50 ml
  4. filtrationThe resultant solid is filtered
  5. custompurified by chromatography on silicic acid
  6. washElution with 97.5% chloroform/2.5% methanol
  7. customgives 2.0 gm
  8. customof 6-methyl-8-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]-2H,4H-oxazolo[5,4,3-ij]quinolin-4-one, recrystallized from acetonitrile, m.p. 262°-264°

Sources & evidence

ORD record
ord-b6ae293e3a8a4819b1bd34340f5ec80f
Source dataset
uspto-grants-1981_02
Patent number
US04251534

Reaction notes

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