Trifluoroacetic acid → HCID 21269512, compound

HRID 2231509Notes

Reaction equation

HRID 2231509 reaction equation
O.Br.[OH:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[OH:14])[CH:10]=[N:9][CH:8]=[CH:7]2.[C:15](OC(=O)C)(=[O:17])[CH3:16].F[C:23](F)(F)[C:24](O)=[O:25]>>[C:15]([O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][C:24](=[O:25])[CH3:23])[CH:10]=[N:9][CH:8]=[CH:7]2)(=[O:17])[CH3:16]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7918Acetic AnhydrideHCID 135574541HCID 135574541, compound

Product 1

HCID 21269512HCID 21269512, compoundYield 93.4%

Procedure

500 mg (1.9 mmol) of 6,7-dihydroxyisoquinoline hydrobromide monohydrate was suspended in 10 ml of trifluoroacetic acid, and 2.0 ml (21 mmol) of acetic anhydride was added thereto at room temperature. The mixture was stirred at the same temperature for 24 hours. The reaction solution was concentrated under reduced pressure. Water and ethyl acetate were added to the residue. Then, the aqueous solution was adjusted to pH 8.0 with a 5% sodium hydrogen carbonate aqueous solution, and extracted with ethyl acetate. The extract was washed with a saturated sodium chloride aqueous solution, then dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain 440 mg (yield: 93.4%) of the above identified compound.

Workup

  1. customat room temperature
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. additionWater and ethyl acetate were added to the residue
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with a saturated sodium chloride aqueous solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customto obtain 440 mg (yield: 93.4%) of the

Sources & evidence

ORD record
ord-b879cfca5551415b8a402f4be4ed4b4c
Source dataset
uspto-grants-1988_11
Patent number
US04782155

Reaction notes

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