N-Iodosuccinimide → 5-Iodo-6-methoxynaphthalene-2-carbonitrile

HRID 1772173Notes

Reaction equation

HRID 1772173 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:13]#[N:14])[CH:7]=[CH:6]2.[I:15]N1C(=O)CCC1=O.C(=O)([O-])O.[Na+]>C(#N)C.C(O)(C(F)(F)F)=O>[I:15][C:4]1[C:3]([O:2][CH3:1])=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][C:8]([C:13]#[N:14])=[CH:9]2

Participants

6

Reactant 3

HCID 120273N-IodosuccinimideHCID 3491736-Methoxynaphthalene-2-carbonitrileHCID 516892Sodium Bicarbonate

Product 1

HCID 1179026645-Iodo-6-methoxynaphthalene-2-carbonitrile

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of 6-methoxynaphthalene-2-carbonitrile (1.0 g, 5.5 mmol), N-iodosuccinimide (1.4 g, 6.0 mmol) in ACN (10 ml) and TFA (125 μl) is stirred at RT for 4 h. A saturated aqueous solution of sodium hydrogencarbonate is added and the mixture extracted with DCM. The combined organic layers are extracted with an aqueous solution of sodium thiosulfate, dried over MgSO4 and concentrated in vacuo. The product is purified by RP HPLC. Yield: 1.68 g (99%). HPLC-MS: tR=1.32 min (METHOD—1).

Workup

  1. extractionthe mixture extracted with DCM
  2. extractionThe combined organic layers are extracted with an aqueous solution of sodium thiosulfate
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe product is purified by RP HPLC

Sources & evidence

ORD record
ord-2d2b54f742be4a319fc19536e0ca3c0d
Source dataset
uspto-grants-2016_02
Patent number
US09249151B2

Reaction notes

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