Hydrochloric Acid → 4-Chloro-2-cyclopropylaniline

HRID 1478803Notes

Reaction equation

HRID 1478803 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8]C(=O)C)=[C:4]([CH:12]2[CH2:14][CH2:13]2)[CH:3]=1.Cl>CCOC(C)=O.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([CH:12]2[CH2:14][CH2:13]2)[CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 118513284N-(4-chloro-2-cyclopropylphenyl)acetamide

Product 1

HCID 183682604-Chloro-2-cyclopropylaniline

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of N-(4-chloro-2-cyclopropylphenyl)acetamide (689 mg, 3.29 mmol) in 2M HCl (aq) (25 ml, 823 mmol) was stirred at 100° C. for 3 hrs and then 90° C. for 16 hrs. The resulting mixture was cooled to RT, diluted with EtOAc and water and the layers separated. The organic layer was extracted with 0.1 M HCl (aq) and the organic portion was discarded. To the combined aqueous portions was added 2M NaOH (aq) until basic and resulting mixture was extracted with EtOAc (2×). The organic extracts were washed with brine, dried over MgSO4, filtered and concentrated under vacuum to give the title compound as a dark yellow oil.

Workup

  1. wait90° C. for 16 hrs
  2. temperatureThe resulting mixture was cooled to RT
  3. customthe layers separated
  4. extractionThe organic layer was extracted with 0.1 M HCl (aq)
  5. additionTo the combined aqueous portions was added 2M NaOH (aq) until basic and
  6. customresulting mixture
  7. extractionwas extracted with EtOAc (2×)
  8. washThe organic extracts were washed with brine
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-c1746f60b5a84bbca83fdb4df99a7c50
Source dataset
uspto-grants-2016_08
Patent number
US09403833B2

Reaction notes

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