Hydrochloric Acid → HCID 68821374, compound

HRID 1811536Notes

Reaction equation

HRID 1811536 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8]C(=O)C)=[C:4]([F:12])[C:3]=1[CH2:13][CH3:14].Cl>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([F:12])[C:3]=1[CH2:13][CH3:14]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69001066HCID 69001066, compound

Product 1

HCID 68821374HCID 68821374, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-(4-chloro-3-ethyl-2-fluorophenyl)acetamide (11.0 g, 51.0 mmol) in MeOH (80 mL) is added concentrated HCl (40 mL) before heating at reflux for 16 hours. The solvent is removed from the cooled reaction under reduced pressure maintaining the water bath below 45° C. The residue is cooled with an ice bath before a 3N NaOH solution is added to adjust pH between 9 and 10. The mixture is extracted with ether and dried over MgSO4. The solvent is removed and the residue is purified through a flash chromatography using a gradient of ether/hexanes to give 4-chloro-3-ethyl-2-fluoroaniline.

Workup

  1. temperaturebefore heating
  2. temperatureat reflux for 16 hours
  3. customThe solvent is removed from the cooled reaction under reduced pressure
  4. temperaturemaintaining the water bath below 45° C
  5. temperatureThe residue is cooled with an ice bath before a 3N NaOH solution
  6. additionis added
  7. extractionThe mixture is extracted with ether
  8. dry with materialdried over MgSO4
  9. customThe solvent is removed
  10. customthe residue is purified through a flash chromatography

Sources & evidence

ORD record
ord-aa78bb78673f403b8335ebcd0cb398f1
Source dataset
uspto-grants-2013_01
Patent number
US08362294B2

Reaction notes

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