Water → 4-Amino-5-iodo-2-methoxybenzoic acid

HRID 1440216Notes

Reaction equation

HRID 1440216 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([O:11][CH3:12])[CH:3]=1.[I:13]N1C(=O)CCC1=O.O>O1CCOCC1>[NH2:1][C:2]1[C:10]([I:13])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([O:11][CH3:12])[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 755994-Amino-o-anisic acidHCID 120273N-Iodosuccinimide

Product 1

HCID 153457254-Amino-5-iodo-2-methoxybenzoic acidYield 49.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred and heated (25° C.) solution of 5 g of 4-amino-2-methoxy benzoic acid in 75 ml of 1,4-dioxane were added 6.9 g of grinded 1-iodo-2,5-pyrrolidinedione. The mixture was stirred in an oil bath at 105° C. for 3 hours. After the addition of 300 ml of water, the crystallized product was filtered off and dried, yielding 4.3 g (48.9%) of 4-amino-5-iodo-2-methoxybenzoic acid; mp. 180.6° C. (interm. 5).

Workup

  1. stirringThe mixture was stirred in an oil bath at 105° C. for 3 hours
  2. filtrationthe crystallized product was filtered off
  3. customdried

Sources & evidence

ORD record
ord-26784b1b304748e4b422a5959718becf
Source dataset
uspto-grants-1996_03
Patent number
US05498618

Reaction notes

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