Iodine chloride → Methyl 4-amino-5-iodo-2-methoxybenzoate

HRID 630418Notes

Reaction equation

HRID 630418 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([O:12][CH3:13])[CH:3]=1.[I:14]Cl>C(O)(=O)C>[NH2:1][C:2]1[C:11]([I:14])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([O:12][CH3:13])[CH:3]=1

Participants

4

Reactant 2

HCID 24640Iodine chlorideHCID 168705Methyl 4-amino-o-anisate

Product 1

HCID 15700587Methyl 4-amino-5-iodo-2-methoxybenzoateYield 88%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of methyl 4-amino-2-methoxybenzoate (13 g, 0.07 mol) in acetic acid (300 mL) was added dropwise a solution of iodine monochloride (11.5 g, 0.07 mol) in acetic acid (50 mL). The mixture was stirred for 1.5 hours at room temperature. The precipitate was filtered and washed with ether. Then was dissolved with bicarbonate 4% and extracted with ethyl acetate. The organic layer was washed with brine, dried and the solvent was removed under reduced pressure giving the title compound as a white solid (88%), which was used in the next step without further purification.

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with ether
  3. dissolutionThen was dissolved with bicarbonate 4%
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. customdried
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-b0d898fe99ca41dcbd16a289f92af956
Source dataset
uspto-grants-2016_04
Patent number
US09315463B2

Reaction notes

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