N-Iodosuccinimide → HCID 50941658, compound

HRID 1919665Notes

Reaction equation

HRID 1919665 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[I:13]N1C(=O)CCC1=O>C(O)(=O)C>[NH2:1][C:2]1[C:3]([I:13])=[CH:4][C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 15049977Methyl 5-Amino-2-methylbenzoate

Product 1

HCID 50941658HCID 50941658, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Methyl 5-amino-2-methylbenzoate (1.0 eq, 3.75 g) was dissolved in acetic acid (70 ml). N-Iodosuccinimide (1.0 eq, 5.27 g) was added portionwise over 60 minutes. The mixture was stirred at room temperature for 30 minutes. Acetic acid was evaporated. The residue was diluted with ethyl acetate (80 ml) and neutralized with saturated sodium carbonate (80 ml). The organic layer was washed with 1M sodium thiosulfate (2×40 ml), then water (2×40 ml) and brine (2×40 ml). The material was purified by flash chromatography on silica gel (gradient 10% to 30% ethyl acetate in hexanes) to provide methyl 5-amino-4-iodo-2-methylbenzoate as a yellow-orange solid (3.19 g, 49% yield). GCMS>95% pure, m/z 291. 1H NMR (400 MHz, DMSO, d6) δ 2.30 (s, 3H), 3.78 (s, 3H), 5.27 (br s, 2H), 7.24 (s, 1H), 7.54 (s, 1H).

Workup

  1. customAcetic acid was evaporated
  2. additionThe residue was diluted with ethyl acetate (80 ml)
  3. washThe organic layer was washed with 1M sodium thiosulfate (2×40 ml)
  4. customThe material was purified by flash chromatography on silica gel (gradient 10% to 30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-a0201ec8e60842d2a9b31af6f543c6b9
Source dataset
uspto-grants-2012_05
Patent number
US08168651B2

Reaction notes

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