Trifluoroacetic acid → HCID 21269512, compound

HRID 1194610Notes

Reaction equation

HRID 1194610 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-ff5954a85e384751a09a0a4c493a3f78
Source dataset
uspto-grants-1989_03
Patent number
US04814328

Reaction notes

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