Hydrochloric Acid → (2-Fluoro-6-iodophenyl)methanamine

HRID 2390043Notes

Reaction equation

HRID 2390043 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([I:10])[C:3]=1[C:4]#[N:5].Cl.C(=O)(O)[O-].[Na+]>O1CCCC1>[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([I:10])[C:3]=1[CH2:4][NH2:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 5227222-Fluoro-6-iodobenzonitrile

Product 1

HCID 68520740(2-Fluoro-6-iodophenyl)methanamineYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under an argon atmosphere, 123 mg of 2-fluoro-6-iodobenzonitrile was dissolved in 2 mL of tetrahydrofuran, and 1.5 mL of a borane/tetrahydrofuran complex was added thereto, followed by stirring under reflux overnight. The reaction liquid was cooled to room temperature, and 2N hydrochloric acid was added thereto, followed by further stirring for 1 hour. After completion of the reaction, to the reaction liquid was added an aqueous sodium bicarbonate solution, followed by extraction with ethyl acetate, and the organic layer was then washed with an aqueous sodium bicarbonate solution and saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure to obtain 87 mg (70%) of 2-fluoro-6-iodobenzylamine as a light yellow oily substance. This product, 68 mg of di-tert-butyl dicarbonate, and 31 mg of triethylamine were dissolved in 1 mL of chloroform, followed by stirring at room temperature for 1 hour. After completion of the reaction, water was added to the reaction liquid, followed by extraction with chloroform. The organic layer was then washed with an aqueous sodium bicarbonate solution and saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue obtained was purified using PLC (n-hexane:ethyl acetate=2:1) to obtain 80 mg (yield 81%) of a title compound as a light yellow solid.

Workup

  1. addition1.5 mL of a borane/tetrahydrofuran complex was added
  2. temperatureunder reflux overnight
  3. customThe reaction liquid
  4. stirringby further stirring for 1 hour
  5. customAfter completion of the reaction
  6. customto the reaction liquid
  7. extractionfollowed by extraction with ethyl acetate
  8. washthe organic layer was then washed with an aqueous sodium bicarbonate solution and saturated brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c55ef78d92ac4ba2a4bc7af948f893ad
Source dataset
uspto-grants-2012_09
Patent number
US08273766B2

Reaction notes

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