N-Iodosuccinimide → 5-Iodo-6-methoxy-3-nitropyridin-2-amine

HRID 505391Notes

Reaction equation

HRID 505391 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([NH2:9])[C:6]([N+:10]([O-:12])=[O:11])=[CH:5][CH:4]=1.[I:13]N1C(=O)CCC1=O>C(O)(=O)C>[I:13][C:4]1[CH:5]=[C:6]([N+:10]([O-:12])=[O:11])[C:7]([NH2:9])=[N:8][C:3]=1[O:2][CH3:1]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 38524282-Amino-6-methoxy-3-nitropyridine

Product 1

HCID 573549285-Iodo-6-methoxy-3-nitropyridin-2-amineYield 99%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A suspension of 6-methoxy-3-nitro-2-pyridineamine (14.6 g, 86.4 mmol) and N-iodosuccinimide (29.2 g, 130 mmol) in acetic acid (280 ml) was stirred at room temperature for 21 hours and 30 minutes. The reaction mixture was concentrated and the residue was dissolved in ethyl acetate and 0.5N sodium hydroxide. The ethyl acetate layer was washed with a saturated sodium bicarbonate solution and a saturated brine solution, dried over anhydrous sodium sulfate, and concentrated. The residue was suspended in hexane, and a resulted precipitate was filtered and washed with hexane, thereby yielding the title compound (25.2 g, 85.5 mmol, 98.9%) as a yellow solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThe ethyl acetate layer was washed with a saturated sodium bicarbonate solution
  4. dry with materiala saturated brine solution, dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. filtrationa resulted precipitate was filtered
  7. washwashed with hexane

Sources & evidence

ORD record
ord-635e35f98e904c50ac3f494a9cf36466
Source dataset
uspto-grants-2010_08
Patent number
US07781452B2

Reaction notes

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