Isopropyl iodide → HCID 18470610, compound

HRID 2228504Notes

Reaction equation

HRID 2228504 reaction equation
I[CH:2]([CH3:4])[CH3:3].[CH3:5][O:6][C:7]1[C:8]([OH:22])=[C:9]([C:14]([N+:19]([O-:21])=[O:20])=[CH:15][C:16]=1[O:17][CH3:18])[C:10]([O:12][CH3:13])=[O:11].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[CH3:5][O:6][C:7]1[C:8]([O:22][CH:2]([CH3:4])[CH3:3])=[C:9]([C:14]([N+:19]([O-:21])=[O:20])=[CH:15][C:16]=1[O:17][CH3:18])[C:10]([O:12][CH3:13])=[O:11]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 10340Sodium CarbonateHCID 18470626HCID 18470626, compound

Product 1

HCID 18470610HCID 18470610, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

2-Iodopropane (0.5 ml, 0.005 mol) was added to a suspension of methyl 3,4-dimethoxy-2-hydroxy-6-nitrobenzoate (1 g, 0.0039 mol) and sodium carbonate (1.6 g, 0.015 mol) in dimethylformamide (15 ml) and the reaction stirred at 60° C. for 2 hours. On cooling, the reaction was concentrated under reduced pressure and the residue partitioned between ethyl acetate (25 ml) and water (25 ml). The aqueous layer was further extracted with ethyl acetate (2×25 ml), the combined organic extracts dried (MgSO4), filtered and evaporated under reduced pressure to give the subtitle compound as a crystalline solid (1.1 g, 74%). 1H-NMR (CDCl3): Γ=1.28 (6H, d), 3.94 (9H, m), 4.72 (1H, m), 7.49 (1H, s).

Workup

  1. temperatureOn cooling
  2. concentrationthe reaction was concentrated under reduced pressure
  3. customthe residue partitioned between ethyl acetate (25 ml) and water (25 ml)
  4. extractionThe aqueous layer was further extracted with ethyl acetate (2×25 ml)
  5. dry with materialthe combined organic extracts dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-5c1f9c20ee204f3fb499c5d472314b72
Source dataset
uspto-grants-2002_07
Patent number
US06417194B1

Reaction notes

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