Water → HCID 118452636, compound

HRID 1773242Notes

Reaction equation

HRID 1773242 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]([F:14])([F:13])[F:12])=[C:6]([C:15]([CH3:17])=[CH2:16])[CH:5]=1)([O-])=O.O>C1(C)C=CC=CC=1.Cl.[Fe]>[CH2:16]=[C:15]([C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][C:7]=1[O:10][C:11]([F:12])([F:14])[F:13])[NH2:1])[CH3:17]

Participants

6

Reactant 2

HCID 962WaterHCID 1184526474-Nitro-2-(prop-1-en-2-yl)-1-(trifluoromethoxy)benzene

Product 1

HCID 118452636HCID 118452636, compoundYield 95.4%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 23925IronCatalystHCID 1140TolueneSolvent

Procedure

To a solution of 4-nitro-2-(prop-1-en-2-yl)-1-(trifluoromethoxy)benzene (275 mg, 1.11 mmol) in toluene (9.85 mL) was added iron (1.24 g, 22.25 mmol) and concentrated HCl (3.38 μL, 0.11 mmol) (3 drops). The mixture was stirred vigorously under reflux and water (0.20 mL, 11.13 mmol) was added and the r×n was stirred at reflux for 2 hr. The crude mixture was filtered through celite and concentrated under reduced pressure. The crude was diluted with EtOAc and dried with Na2SO4, filtered and concentrated under reduced pressure to give 3-(prop-1-en-2-yl)-4-(trifluoromethoxy)aniline (230 mg). LCMS retention time=1.46 minutes (LC method 5); MS (m+1)=218.2.

Workup

  1. temperatureunder reflux
  2. stirringthe r×n was stirred
  3. temperatureat reflux for 2 hr
  4. filtrationThe crude mixture was filtered through celite and
  5. concentrationconcentrated under reduced pressure
  6. additionThe crude was diluted with EtOAc
  7. dry with materialdried with Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3a87f898d71d47efb17e856a27b9102b
Source dataset
uspto-grants-2016_02
Patent number
US09255093B2

Reaction notes

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