Hydrochloric Acid → 1000590-77-1

HRID 1811528Notes

Reaction equation

HRID 1811528 reaction equation
[Cl:1][C:2]1[C:7]([I:8])=[C:6]([Cl:9])[CH:5]=[CH:4][C:3]=1[NH:10]C(=O)C.Cl>CO>[Cl:1][C:2]1[C:7]([I:8])=[C:6]([Cl:9])[CH:5]=[CH:4][C:3]=1[NH2:10]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68823443HCID 68823443, compound

Product 1

HCID 688212971000590-77-1

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-(2,4-dichloro-3-iodophenyl)acetamide (40.0 g, 121 mmol) in MeOH (100 mL) is added concentrated HCl (50 mL). The mixture is stirred and heated at reflux for 18 hours. The mixture is cooled and the solvents were removed under reduced pressure (water bath below 45° C.). The residue is cooled with an ice bath and 3N NaOH solution was added to adjust the pH to between 9 and 10. The mixture is extracted with ether and dried over MgSO4. The solvents were removed and the residue is purified through a flash chromatographic column with a gradient of hexanes/ether to give 2,4-dichloro-3-iodoaniline.

Workup

  1. temperatureheated
  2. temperatureat reflux for 18 hours
  3. temperatureThe mixture is cooled
  4. customthe solvents were removed under reduced pressure (water bath below 45° C.)
  5. temperatureThe residue is cooled with an ice bath
  6. addition3N NaOH solution was added
  7. extractionThe mixture is extracted with ether
  8. dry with materialdried over MgSO4
  9. customThe solvents were removed
  10. customthe residue is purified through a flash chromatographic column with a gradient of hexanes/ether

Sources & evidence

ORD record
ord-2f3035ea8309400097aaaa670f4aabfc
Source dataset
uspto-grants-2013_01
Patent number
US08362294B2

Reaction notes

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