Sulfuric Acid → HCID 86639059, compound

HRID 1019568Notes

Reaction equation

HRID 1019568 reaction equation
S(=O)(=O)(O)O.[F:6][C:7]([F:21])([F:20])[C:8]1[N:13]=[C:12]2[CH:14]=[C:15]([C:17]([OH:19])=[O:18])[NH:16][C:11]2=[CH:10][CH:9]=1>C(O)C>[F:21][C:7]([F:6])([F:20])[C:8]1[N:13]=[C:12]2[CH:14]=[CH:15][NH:16][C:11]2=[CH:10][CH:9]=1.[CH3:14][CH2:15][C:17]([O-:19])=[O:18]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 573558695-(Trifluoromethyl)-1H-pyrrolo[3,2-b]pyridine-2-carboxylic acid

Product 1

HCID 86639059HCID 86639059, compoundYield 168.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1 mL (18.71 mmol) of concentrated sulfuric acid is added to a solution of 0.2 g (0.87 mmol) of 5-trifluoromethyl-pyrrolo[3,2-b]pyridine-2-carboxylic acid, obtained in Stage 10.2, in 10 mL of ethanol. It is stirred under reflux for 20 hours then the solution is cooled, and concentrated at reduced pressure. The resultant residue is then taken up in 50 mL of dichloromethane then washed successively with 20 mL of a saturated aqueous solution of sodium bicarbonate, 40 mL of water and 20 mL of saturated aqueous solution of sodium chloride, dried over sodium sulfate and then concentrated at reduced pressure. We obtain 0.19 g of product, which is used as it is in the next stage.

Workup

  1. temperatureunder reflux for 20 hours
  2. temperaturethe solution is cooled
  3. concentrationconcentrated at reduced pressure
  4. washthen washed successively with 20 mL of a saturated aqueous solution of sodium bicarbonate, 40 mL of water and 20 mL of saturated aqueous solution of sodium chloride
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-90bc882821a44659aff3ab672679eb63
Source dataset
uspto-grants-2014_05
Patent number
US08716273B2

Reaction notes

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