Iodine → 4-hydroxy-3-iodo-N-methoxy-N-methylbenzamide

HRID 494828Notes

Reaction equation

HRID 494828 reaction equation
[OH:1][C:2]1[CH:13]=[CH:12][C:5]([C:6]([N:8]([O:10][CH3:11])[CH3:9])=[O:7])=[CH:4][CH:3]=1.[I:14]I>[OH-].[NH4+].O>[OH:1][C:2]1[CH:13]=[CH:12][C:5]([C:6]([N:8]([O:10][CH3:11])[CH3:9])=[O:7])=[CH:4][C:3]=1[I:14]

Participants

5

Reactant 2

HCID 807IodineHCID 113897574-Hydroxy-N-methoxy-N-methylbenzamide

Product 1

HCID 117712104-hydroxy-3-iodo-N-methoxy-N-methylbenzamideYield 67%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14923Ammonium HydroxideSolvent

Procedure

The product from Example 71C (10.3 g, 56.84 mmol) in concentrated ammonium hydroxide (400 mL) was stirred at 25° C. for 15 minutes and then treated with KI (45.96 g, 276.83 mmol) and I2 (14.43 g, 56.84 mmol) in water (65 mL). After stirring at room temperature for 16 hours, the solvent was removed under reduced pressure and the residue was redissolved in DCM (500 mL) and washed with water (350 mL×2). The organic phase was dried, filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel using 90% CH2Cl2, 10% MeOH, to provide the title compound as a white solid (11.6 g, 67% yield). 1HNMR (300 MHz, CD3OD) δ 3.32 (s, 3H), 3.59 (s, 3H), 6.83 (d, 1H, J=8.9 Hz). 7.58 (d, 1H, J=8.9 Hz), 8.06 (s, 1H); MS (DCI) m/z 308 (M+H)+, 325 (M+NH4)+.

Workup

  1. customthe solvent was removed under reduced pressure
  2. dissolutionthe residue was redissolved in DCM (500 mL)
  3. washwashed with water (350 mL×2)
  4. customThe organic phase was dried
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified by flash chromatography on silica gel using 90% CH2Cl2, 10% MeOH

Sources & evidence

ORD record
ord-58c1dbc3cf0d483db8f899c6afc9abc1
Source dataset
uspto-grants-2009_05
Patent number
US07538138B2

Reaction notes

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