Hydrochloric Acid → Methyl 2-amino-4-iodobenzoate

HRID 2293912Notes

Reaction equation

HRID 2293912 reaction equation
C([NH:4][C:5]1[CH:13]=[C:12]([I:14])[CH:11]=[CH:10][C:6]=1[C:7]([OH:9])=[O:8])(=O)C.Cl.[CH3:16]O>>[NH2:4][C:5]1[CH:13]=[C:12]([I:14])[CH:11]=[CH:10][C:6]=1[C:7]([O:9][CH3:16])=[O:8]

Participants

4

Reactant 3

HCID 313Hydrochloric Acid2×HCID 887MethanolHCID 142335972-Acetamido-4-iodobenzoic acid

Product 1

HCID 18929930Methyl 2-amino-4-iodobenzoate

Procedure

A solution of 16.1 g of 2-acetylamino-4-iodobenzoic acid (m.p. 233°-5° C; synthesized in accordance with U.S. Pat. No. 4,762,838) in 325 ml of absolute methanol is saturated at 0° C. with dry hydrogen chloride gas. The mixture is heated to the boil for 15 hours, cooled to room temperature, resaturated using dry hydrogen chloride gas, and allowed to stand at room temperature for 24 hours. The solvent is evaporated in vacuo, the residue is taken up in dichloromethane, and the organic phase is washed with a saturated aqueous sodium hydrogen carbonate solution until free from acid. The organic phase is dried over Na2 SO4, and evaporated in vacuo. This gives 13.8 g of methyl 2-amino-4-iodobenzoate of m.p. 63°-7° C.

Workup

  1. customsynthesized in accordance with U.S
  2. temperatureThe mixture is heated to the boil for 15 hours
  3. customThe solvent is evaporated in vacuo
  4. washthe organic phase is washed with a saturated aqueous sodium hydrogen carbonate solution until free from acid
  5. customThe organic phase is dried over Na2 SO4
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-122a748858be4ce4be0c7088f5507ef0
Source dataset
uspto-grants-1997_11
Patent number
US05688745

Reaction notes

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