Trifluoroacetic acid → 3-Methoxyaniline

HRID 1481671Notes

Reaction equation

HRID 1481671 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:15]2C(C(=O)NC3C=CC=CC=3)=CN=C(S(C)(=O)=O)N=2)[CH:9]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:15][O:14][C:10]1[CH:9]=[C:8]([CH:13]=[CH:12][CH:11]=1)[NH2:7]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59174704HCID 59174704, compound

Product 1

HCID 108243-MethoxyanilineYield 287.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 7 (0.15 g, 0.24 mmol) in dry CH2Cl2 (5 mL) at 0° C. was added CF3COOH (1.5 mL) and the reaction mixture was stirred at 0° C. for 30 min. The reaction was allowed to come to rt and stirred at it for 1 h. It was concentrated under reduced pressure and the residue was quenched with NaHCO3 solution (3 mL) and extracted with EtOAc (3×25 mL). The combined EtOAc extract was washed with water (20 mL), brine (10 mL) and dried over Na2SO4 and concentrated under reduced pressure to give 8 (0.085 g, 86.7%) as a white solid.

Workup

  1. customto come to rt
  2. stirringstirred at it for 1 h
  3. concentrationIt was concentrated under reduced pressure
  4. customthe residue was quenched with NaHCO3 solution (3 mL)
  5. extractionextracted with EtOAc (3×25 mL)
  6. extractionThe combined EtOAc extract
  7. washwas washed with water (20 mL), brine (10 mL)
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-96dbab8a45e94b0e930763088dbfabd1
Source dataset
uspto-grants-2016_08
Patent number
US09409921B2

Reaction notes

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