2-Amino-3-methylbenzoic acid → 2-Amino-5-iodo-3-methylbenzoic Acid

HRID 1983068Notes

Reaction equation

HRID 1983068 reaction equation
[NH2:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[I:12]N1C(=O)CCC1=O>CN(C)C=O.O>[NH2:1][C:2]1[C:10]([CH3:11])=[CH:9][C:8]([I:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 2

HCID 781012-Amino-3-methylbenzoic acidHCID 120273N-Iodosuccinimide

Product 1

HCID 112312332-Amino-5-iodo-3-methylbenzoic AcidYield 43.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

2-Amino-3-methylbenzoic acid (10 g, 66 mmol) was dissolved in 70 mL of N,N-dimethyl-formamide (DMF) and treated with N-iodosuccinimide (16.4 g, 73 mmol). The mixture was heated at 60° C. for 17 hours and allowed to cool to 25° C. The mixture was diluted with water (150 mL and filtered. The air-dried solid was dissolved in ethyl acetate (200 mL) and dried over magnesium sulfate. Evaporation of the solvent provided the title compound of Step A (7.95 g). 1H NMR (CDCl3): δ 7.87 (1H), 7.44 (1H), 2.09 (3H).

Workup

  1. temperatureto cool to 25° C
  2. filtrationfiltered
  3. dissolutionThe air-dried solid was dissolved in ethyl acetate (200 mL)
  4. dry with materialdried over magnesium sulfate
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-d599d6f772e342368f8e33293d0af326
Source dataset
uspto-grants-2009_06
Patent number
US07541377B2

Reaction notes

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