Dimethylformamide → HCID 58508922, compound

HRID 454521Notes

Reaction equation

HRID 454521 reaction equation
[H-].[Na+].[CH3:3]N(C)C=O.[CH2:8]([NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]1[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[C:19]([N+:27]([O-:29])=[O:28])[CH:18]=1)[CH3:9].CI>C(OCC)C.O>[CH2:8]([N:10]([CH3:3])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]1[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[C:19]([N+:27]([O-:29])=[O:28])[CH:18]=1)[CH3:9]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodide2×HCID 24758Sodium hydrideHCID 66990423HCID 66990423, compound

Product 1

HCID 58508922HCID 58508922, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

Under ice-cooling, 60% sodium hydride (54 mg) was added to an N,N-dimethylformamide (3.0 mL) solution of methyl 4-(2-(ethylamino)phenyl)-2-nitrobenzoate (0.27 g), followed by stirring at the same temperature for 5 minutes and then at room temperature for 15 minutes. Methyl iodide (0.083 mL) was added to the reaction mixture under ice-cooling, followed by stirring at room temperature for 1 hour and then at 50° C. for 1 hour. The reaction mixture was cooled to room temperature, and then methyl iodide (0.11 mL) was added thereto, followed by stirring at 40 to 50° C. for 2 hours. The reaction mixture was cooled to room temperature, and then water and diethyl ether were added thereto. The organic layer was separated, washed with a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride sequentially, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: 99-95% hexane/ethyl acetate] to obtain 0.12 g of methyl 4-(2-((ethyl)(methyl)amino)phenyl)-2-nitrobenzoate as a yellow oily substance.

Workup

  1. temperatureUnder ice-cooling
  2. waitat room temperature for 15 minutes
  3. temperaturecooling
  4. stirringby stirring at room temperature for 1 hour
  5. waitat 50° C. for 1 hour
  6. stirringby stirring at 40 to 50° C. for 2 hours
  7. temperatureThe reaction mixture was cooled to room temperature
  8. customThe organic layer was separated
  9. washwashed with a saturated aqueous solution of sodium bicarbonate
  10. dry with materiala saturated aqueous solution of sodium chloride sequentially, and dried over anhydrous magnesium sulfate
  11. customthe solvent was evaporated under reduced pressure
  12. customThe obtained residue was purified by silica gel column chromatography [eluent: 99-95% hexane/ethyl acetate]

Sources & evidence

ORD record
ord-400756b371d74edf859b88045ceb047a
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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