Methanol → 3-(3,4-Dimethoxyanilino)butanoic acid

HRID 597193Notes

Reaction equation

HRID 597193 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][C:17]=1[O:18][CH3:19])[NH:6][CH:7]([CH3:14])[CH2:8][C:9]([O:11]CC)=[O:10].[OH-].[Na+].CO>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][C:17]=1[O:18][CH3:19])[NH:6][CH:7]([CH3:14])[CH2:8][C:9]([OH:11])=[O:10]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 21439734Ethyl 3-(3,4-dimethoxyanilino)butanoate

Product 1

HCID 214397393-(3,4-Dimethoxyanilino)butanoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 54-g sample of the unpurified ester product of Example 2 was combined with 17.5 g of sodium hydroxide, 550 ml of methanol and 130 ml of water, and refluxed for 1.5 hrs. The reaction mixture was cooled, concentrated under reduced pressure, diluted with water and neutralized with 6N hydrochloric acid to give an oily mixture which was extracted with chloroform. The combined organic extracts were dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 48 g of an oily product. This material was used in the next step without further purification.

Workup

  1. temperaturerefluxed for 1.5 hrs
  2. temperatureThe reaction mixture was cooled
  3. concentrationconcentrated under reduced pressure
  4. additiondiluted with water and neutralized with 6N hydrochloric acid
  5. customto give an oily mixture which
  6. extractionwas extracted with chloroform
  7. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-69595695bf724381ba0bd4fd93b2a8e6
Source dataset
uspto-grants-1977_03
Patent number
US04013662

Reaction notes

Loading…