Hydrochloric Acid → 4-(Trifluoromethyl)-1H-indole

HRID 2278639Notes

Reaction equation

HRID 2278639 reaction equation
CN(C)/[CH:3]=[CH:4]/[C:5]1[C:10]([C:11]([F:14])([F:13])[F:12])=[CH:9][CH:8]=[CH:7][C:6]=1[N+:15]([O-])=O.Cl>C(O)(=O)C.[Fe]>[F:14][C:11]([F:12])([F:13])[C:10]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:5]=1[CH:4]=[CH:3][NH:15]2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 57753441Ethenamine, N,N-dimethyl-2-[2-nitro-6-(trifluoromethyl)phenyl]-, (1E)-

Product 1

HCID 198037034-(Trifluoromethyl)-1H-indoleYield 112.3%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

850 mg of powdered iron are added to a solution of 1.2 g of dimethyl[(E)-2-(2-nitro-6-trifluoromethylphenyl)vinyl]amine in 30 ml of acetic acid. The reaction mixture is refluxed for 16 hours and then poured into a solution of hydrochloric acid (HCl, 2N), and extracted with ethyl acetate. The organic phases are washed with a 10% sodium carbonate solution and then with a saturated NaCl solution, dried over magnesium sulfate, filtered, and concentrated under reduced pressure so as to give 959 mg of 4-trifluoromethyl-1H-indole which is used in the next step.

Workup

  1. temperatureThe reaction mixture is refluxed for 16 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic phases are washed with a 10% sodium carbonate solution
  4. dry with materialwith a saturated NaCl solution, dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure so as

Sources & evidence

ORD record
ord-38d73d714efe44d180f842daa7d47eb9
Source dataset
uspto-grants-2015_09
Patent number
US09133168B2

Reaction notes

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