Acetic Anhydride → Methyl 4-acetamido-3-iodobenzoate

HRID 1514924Notes

Reaction equation

HRID 1514924 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([I:11])[CH:5]=1.[C:13](OC(=O)C)(=[O:15])[CH3:14]>C(O)(=O)C>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:13](=[O:15])[CH3:14])=[C:6]([I:11])[CH:5]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 4104649Methyl 4-amino-3-iodobenzoate

Product 1

HCID 15304890Methyl 4-acetamido-3-iodobenzoate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of the crude 4-amino-3-iodo-benzoic acid methyl ester in 20 mL of acetic acid was added acetic anhydride (1.25 mL). The reaction was heated at 60° C. for 1 h. The reaction mixture was quenched with water, extracted with ethyl acetate, dried over Na2SO4, and concentrated in vacuo. Purification by flash chromatography (SiO2, 1:3 EtOAc/Hexane) afforded 4-acetylamino-3-iodo-benzoic acid methyl ester: MS (m/z) 320.0 (M+1).

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customPurification by flash chromatography (SiO2, 1:3 EtOAc/Hexane)

Sources & evidence

ORD record
ord-5e00d94141074466ae818105f78c64b4
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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