Hydrochloric Acid → HCID 18621716, compound

HRID 1861921Notes

Reaction equation

HRID 1861921 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[K].[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][C:16]=1[CH2:17]Br.O.Cl>CN(C)C=O.C(OCC)(=O)C>[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][C:16]=1[CH2:17][N:5]1[C:1](=[O:11])[C:2]2=[CH:10][CH:9]=[CH:8][CH:7]=[C:3]2[C:4]1=[O:6]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 775162-(Bromomethyl)-1-methoxy-4-nitrobenzeneHCID 24194345Phthalimide potassium salt

Product 1

HCID 18621716HCID 18621716, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Potassium phthalimide (836 mg) was added to a solution of 2-methoxy-5-nitrobenzyl bromide (1.01 g) in dimethylformamide (41 ml) and stirred at room temperature for 10 minutes. Water and 2 N HCl were added to the reaction mixture and extraction was performed with ethyl acetate; then, the organic layer was washed successively with a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, dried with anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was washed successively with ethyl acetate and hexane to give 1.2 g of the titled compound (yield, 94%).

Workup

  1. washthen, the organic layer was washed successively with a saturated aqueous sodium bicarbonate solution
  2. dry with materiala saturated aqueous sodium chloride solution, dried with anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. washThe resulting residue was washed successively with ethyl acetate and hexane

Sources & evidence

ORD record
ord-11c046887058484aa12ab4516120ba7e
Source dataset
uspto-grants-2003_03
Patent number
US06534546B1

Reaction notes

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