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

HRID 1098302Notes

Reaction equation

HRID 1098302 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 862.5 mg (12.5 mmol) of sodium nitrite were added at 0° C. to an acetic acid solution (15 ml) containing 1.52 g (5.0 mmol) of the 7-amino-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one obtained in Example 38. The obtained mixture was stirred for 30 minutes. Thereafter, 2.62 g (17.5 mmol) of sodium iodide and 952.3 mg (5.0 mmol) of copper iodide (I) were added to the reaction solution, and the obtained mixture was stirred at 80° C. for 1 hour. Thereafter, 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), and was then washed with a sodium thiosulfate aqueous solution, so as to obtain 1.87 g (90%) of 7-iodo-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one in the form of a light yellow solid.

Workup

  1. stirringthe obtained mixture was stirred at 80° C. for 1 hour
  2. temperatureThereafter, the 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. washwas then washed with a sodium thiosulfate aqueous solution

Sources & evidence

ORD record
ord-d8ad36eec38e47068b3cfc0fc2b05e45
Source dataset
uspto-grants-2012_03
Patent number
US08143274B2

Reaction notes

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