Trifluoroacetic acid → 5-(Cyclopent-1-en-1-yl)-2-nitroaniline

HRID 2201684Notes

Reaction equation

HRID 2201684 reaction equation
[C:1]1([C:6]2[CH:7]=[CH:8][C:9]([N+:20]([O-:22])=[O:21])=[C:10]([NH:12]C(=O)OC(C)(C)C)[CH:11]=2)[CH2:5][CH2:4][CH2:3][CH:2]=1.C(O)(C(F)(F)F)=O>ClCCl>[C:1]1([C:6]2[CH:7]=[CH:8][C:9]([N+:20]([O-:22])=[O:21])=[C:10]([CH:11]=2)[NH2:12])[CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71007338Tert-butyl (5-(cyclopent-1-en-1-yl)-2-nitrophenyl)carbamate

Product 1

HCID 867125235-(Cyclopent-1-en-1-yl)-2-nitroanilineYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl (5-(cyclopent-1-en-1-yl)-2-nitrophenyl)carbamate (4.3 g, 14.13 mmol, 1.0 equiv.) in dichloromethane (50 mL) was added TFA (10 mL) at room temperature. The reaction mixture was stirred at room temperature for 2 h. The reaction was then evaporated under reduced pressure. The crude residue was quenched with a saturated solution of sodium bicarbonate. The product was extracted with ethyl acetate, washed with water and brine, dried, filtered and concentrated under reduced pressure. The crude residue was purified by column chromatography (silica gel, 60% EtOAc/hexanes) to give 5-(cyclopent-1-en-1-yl)-2-nitroaniline (2.5 g, 87% yield).

Workup

  1. customThe reaction was then evaporated under reduced pressure
  2. customThe crude residue was quenched with a saturated solution of sodium bicarbonate
  3. extractionThe product was extracted with ethyl acetate
  4. washwashed with water and brine
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude residue was purified by column chromatography (silica gel, 60% EtOAc/hexanes)

Sources & evidence

ORD record
ord-179a158600e14900b8b2b8757bd6eb20
Source dataset
uspto-grants-2016_06
Patent number
US09365498B2

Reaction notes

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