Ethyl Acetate → 2-(2,4-Dichlorophenoxy)aniline

HRID 446856Notes

Reaction equation

HRID 446856 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N+:16]([O-])=O.C(OCC)(=O)C>>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[NH2:16]

Participants

3

Reactant 2

HCID 8857Ethyl AcetateHCID 7759752,4-Dichloro-1-(2-nitrophenoxy)benzene

Product 1

HCID 968292-(2,4-Dichlorophenoxy)anilineYield 99%

Procedure

To a stirred solution of 2,4-dichloro-1-(2-nitro-phenoxy)-benzene (3.5 g, 12.32 mmol) in ethyl acetate (60 mL) stannous chloride dihydrate (13.89 g, 61.6 mmol) was added and the mixture was refluxed for 2 h before it was quenched with saturated sodium hydrogencarbonate solution (192 mL). The organic phase was separated and the aqueous phase was washed several times with ethyl acetate. The combined extracts were dried over sodium sulfate, filtered and concentrated in vacuo to yield 3.1 g (99%) of the title compound as a yellowish oil: MS (EI) 255.2 (MH+).

Workup

  1. temperaturethe mixture was refluxed for 2 h before it
  2. customwas quenched with saturated sodium hydrogencarbonate solution (192 mL)
  3. customThe organic phase was separated
  4. washthe aqueous phase was washed several times with ethyl acetate
  5. dry with materialThe combined extracts were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4b43fd7ea4a54bb6a4047344a38d7ff1
Source dataset
uspto-grants-2013_07
Patent number
US08481527B2

Reaction notes

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