N-Iodosuccinimide → 3-Ethyl-5-iodo-6-methyl-pyridin-2-ylamine

HRID 1438269Notes

Reaction equation

HRID 1438269 reaction equation
[NH2:1][C:2]1[C:7]([CH2:8][CH3:9])=[CH:6][CH:5]=[C:4]([CH3:10])[N:3]=1.[I:11]N1C(=O)CCC1=O>CN(C=O)C>[CH2:8]([C:7]1[C:2]([NH2:1])=[N:3][C:4]([CH3:10])=[C:5]([I:11])[CH:6]=1)[CH3:9]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 30163113-Ethyl-6-methylpyridin-2-amine

Product 1

HCID 587641003-Ethyl-5-iodo-6-methyl-pyridin-2-ylamineYield 81.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-amino-3-ethyl-6-methylpyridine (3.00 g, 21.6 mmol) in DMF (100 mL) was added N-iodosuccinimide (4.86 g, 21.6 mmol). The mixture was stirred in the dark for 15 hours and then partitioned between Et2O and H2O. The organic layer was washed with brine, dried over MgSO4, and concentrated to yield a brown solid (4.6 g, 79%). 1H NMR (300 MHz, CDCl3): δ 1.19 (t, J=7.5 Hz, 3H), 2.35 (q, J=7.4 Hz, 2H), 2.49 (s, 3H), 4.44 (s, 2H), 7.52 (s, 1H).

Workup

  1. custompartitioned between Et2O and H2O
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1d9c81de7af343b880563b4ca988431c
Source dataset
uspto-grants-2009_11
Patent number
US07622605B2

Reaction notes

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