Sodium hydride → N-1,3-Benzodioxol-5-ylglycine methyl ester

HRID 483811Notes

Reaction equation

HRID 483811 reaction equation
[CH2:1]1[O:10][C:9]2[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=2[O:2]1.[H-].[Na+].Br[CH2:14][C:15]([O:17][CH3:18])=[O:16]>O1CCCC1>[CH2:1]1[O:10][C:9]2[CH:8]=[CH:7][C:5]([NH:6][CH2:14][C:15]([O:17][CH3:18])=[O:16])=[CH:4][C:3]=2[O:2]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 843101,3-Benzodioxol-5-amine

Product 1

HCID 893855N-1,3-Benzodioxol-5-ylglycine methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3,4-Methylenedioxyaniline (30.7 g) was dissolved in 300 ml of dry tetrahydrofuran, followed by the addition of 10.7 g of sodium hydride (in oil, 60%) and 22.7 ml of methyl bromoacetate under ice cooling. Under an argon stream, the resultant mixture was stirred at room temperature for 2 days. The reaction mixture was extracted with ether. The organic layer so obtained was washed with water, shaken together with a saturated aqueous NaCl solution and then dried over anhydrous sodium sulfate. The solvent was distilled off, whereby reddish brown crystals were obtained. The crude crystals were decolored and then recrystallized from methanol, whereby 28.0 g of methyl 2-[N-(3,4-methylenedioxyphenyl)amino]acetate were obtained.

Workup

  1. extractionThe reaction mixture was extracted with ether
  2. customThe organic layer so obtained
  3. washwas washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off
  6. customwhereby reddish brown crystals were obtained
  7. customrecrystallized from methanol

Sources & evidence

ORD record
ord-ec82e72ad5e94b39aed067ddc3d17b6a
Source dataset
uspto-grants-1993_07
Patent number
US05227398

Reaction notes

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