Sulfuric Acid → 7-iodo-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one

HRID 1162893Notes

Reaction equation

HRID 1162893 reaction equation
S(=O)(=O)(O)O.N([O-])=O.[Na+].N[C:11]1[CH:20]=[C:19]2[C:14]([CH:15]=[C:16]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:28]([F:31])([F:30])[F:29])[NH:17][C:18]2=[O:21])=[CH:13][CH:12]=1.[I-:32].[Na+].C(=O)(O)[O-].[Na+]>[Cu](I)I.C(O)(=O)C>[I:32][C:11]1[CH:20]=[C:19]2[C:14]([CH:15]=[C:16]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:28]([F:31])([F:30])[F:29])[NH:17][C:18]2=[O:21])=[CH:13][CH:12]=1

Participants

8

Reactant 5

HCID 1118Sulfuric AcidHCID 5238Sodium IodideHCID 516892Sodium BicarbonateHCID 231567387-amino-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-oneHCID 23668193Sodium Nitrite

Product 1

HCID 231568037-iodo-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-oneYield 90.1%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 176Acetic AcidSolvent

Procedure

A 1 N sulfuric acid aqueous solution (30 ml) and sodium nitrite (862.5 mg, 12.5 mmol) were added at 0° C. to an acetic acid solution (15 ml) that contained the 7-amino-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one (1.52 g, 5.0 mmol) obtained in step C, and the obtained mixture was stirred for 30 minutes. Thereafter, sodium iodide (2.62 g, 17.5 mmol) and copper iodide (I) (952.3 mg, 5.0 mmol) were added to the reaction solution, and the obtained mixture was stirred at 80° C. for 1 hour. The reaction solution was cooled, and a saturated sodium bicarbonate aqueous solution was added thereto, followed by extraction with ethyl acetate. The extract was washed with a saturated saline solution, and was then dried over anhydrous sodium sulfate, followed by concentration. The obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4 to 1:2). The resultant was washed with a sodium thiosulfate aqueous solution, so as to obtain 7-iodo-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one (1.87 g; yield: 90%) in the form of a pale yellow solid.

Workup

  1. stirringthe obtained mixture was stirred at 80° C. for 1 hour
  2. temperatureThe reaction solution was cooled
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe extract was washed with a saturated saline solution
  5. dry with materialwas then dried over anhydrous sodium sulfate
  6. concentrationfollowed by concentration
  7. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4 to 1:2)
  8. washThe resultant was washed with a sodium thiosulfate aqueous solution

Sources & evidence

ORD record
ord-234ea6f55e5240a3a57bcb786315ec86
Source dataset
uspto-grants-2010_10
Patent number
US07820693B2

Reaction notes

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