Sodium Hydroxide → HCID 57847019, compound

HRID 550272Notes

Reaction equation

HRID 550272 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][N:5]([CH3:17])[C:6]1[CH:16]=[CH:15][C:9]([C:10]([O:12]CC)=[O:11])=[CH:8][CH:7]=1.[OH-].[Na+]>CO>[CH3:1][O:2][CH2:3][CH2:4][N:5]([CH3:17])[C:6]1[CH:16]=[CH:15][C:9]([C:10]([OH:12])=[O:11])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57847047HCID 57847047, compound

Product 1

HCID 57847019HCID 57847019, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution (10 ml) of ethyl 4-[(2-methoxyethyl) (methyl)amino]benzoate (467 mg, 1.97 mmol) in methanol was added 1M aqueous sodium hydroxide solution (10 ml), and the mixture was stirred at 50° C. for 3 hrs. The reaction mixture was concentrated under reduced pressure, and water and diethyl ether were added to the residue. The organic layer was separated. The aqueous layer was neutralized with 1M hydrochloric acid (10 ml) and extracted with ethyl acetate. The extract was dried over anhydrous MgSO4 and concentrated under reduced pressure to give the title compound (340 mg, 82%) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and water and diethyl ether
  2. additionwere added to the residue
  3. customThe organic layer was separated
  4. extractionextracted with ethyl acetate
  5. dry with materialThe extract was dried over anhydrous MgSO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6c8a642873cf4aa7a2d206329f4cc96b
Source dataset
uspto-grants-2011_05
Patent number
US07943770B2

Reaction notes

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