Water → 2-Amino-5-iodoisophthalic acid

HRID 641964Notes

Reaction equation

HRID 641964 reaction equation
[I:1]Cl.[NH2:3][C:4]1[C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7].O>CC(O)=O>[NH2:3][C:4]1[C:12]([C:13]([OH:15])=[O:14])=[CH:11][C:10]([I:1])=[CH:9][C:5]=1[C:6]([OH:8])=[O:7]

Participants

5

Reactant 3

HCID 962WaterHCID 24640Iodine chlorideHCID 2929162-Aminoisophthalic acid

Product 1

HCID 670430602-Amino-5-iodoisophthalic acidYield 87.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of iodine monochloride (0.9 g) in glacial AcOH (1.7 ml) was added dropwise over 15 minutes to a stirred solution of 2-aminoisophthalic acid (1 g) in glacial AcOH (6.9 ml) at room temperature. The mixture was stirred for 2 hours and then poured into water (70 ml). The resultant orange solid was isolated by filtration, washed with water, diluted with MeOH and concentrated to yield 2-amino-5-iodoisophthalic acid (1.48 g); Mass Spectrum: M+H+ 308.

Workup

  1. customThe resultant orange solid was isolated by filtration
  2. washwashed with water
  3. additiondiluted with MeOH
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-eab42f08c9de4d9cbf90b00ce9d16949
Source dataset
uspto-grants-2010_04
Patent number
US07696215B2

Reaction notes

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