Benzoic acid, 3-amino-, methyl ester → Methyl 3-amino-4-iodobenzoate

HRID 1514927Notes

Reaction equation

HRID 1514927 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[Cl-].[Cl-].[IH2+:14].C([N+](C)(C)C)C1C=CC=CC=1>C(O)(=O)C>[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[I:14])[C:5]([O:7][CH3:8])=[O:6]

Participants

4

Reactant 2

HCID 78274Benzoic acid, 3-amino-, methyl esterHCID 86651265HCID 86651265, compound

Product 1

HCID 21628210Methyl 3-amino-4-iodobenzoate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of methyl 3-aminobenzoate (5.0 g, 33.1 mmol) and benzyltrimethylammonium iodonium dichloride (11.51 g, 33.1 mmols) in acetic acid (20 mL) was stirred at ambient temperature for 18 h. The mixture was concentrated, then poured into ethyl acetate and extracted with aq. NaOH until washes remained basic. The washes were back-extracted with ethyl acetate and the combined ethyl acetate layers were dried, filtered, and the solvent was removed under reduced pressure. The residue was chromatographed on silica gel using a gradient of 0-40% heptane/ethyl acetate to afford methyl 3-amino-4-iodobenzoate.

Workup

  1. concentrationThe mixture was concentrated
  2. additionpoured into ethyl acetate
  3. extractionextracted with aq. NaOH until washes
  4. extractionThe washes were back-extracted with ethyl acetate
  5. dry with materialthe combined ethyl acetate layers were dried
  6. filtrationfiltered
  7. customthe solvent was removed under reduced pressure
  8. customThe residue was chromatographed on silica gel using a gradient of 0-40% heptane/ethyl acetate

Sources & evidence

ORD record
ord-a360a0d97cf0419d9a7ace09c01d0a20
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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