Ethyl bromoacetate → Ethyl 2-(1,3-benzodioxol-5-ylamino)acetate

HRID 2093112Notes

Reaction equation

HRID 2093112 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([NH2:10])=[CH:9][C:4]=2[O:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[CH3:17][CH2:18][O:19][C:20]([CH2:22]Br)=[O:21]>CN(C=O)C>[CH2:18]([O:19][C:20](=[O:21])[CH2:22][NH:10][C:8]1[CH:7]=[CH:6][C:5]2[O:1][CH2:2][O:3][C:4]=2[CH:9]=1)[CH3:17]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 843101,3-Benzodioxol-5-amine

Product 1

HCID 745625Ethyl 2-(1,3-benzodioxol-5-ylamino)acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of Benzo[1,3]dioxol-5-ylamine (1.2 eq.) and potassium carbonate (2.2 eq.) in DMF at 0° C. was added ethyl bromo acetate and stirred at room temperature for overnight. Reaction was then quenched with water and extracted with ethyl acetate, dried over sodium sulphate and concentrated under reduced pressure to afford crude product, which, on purification by column chromatography afforded the (Benzo[1,3]dioxol-5-ylamino)-acetic acid ethyl ester.

Workup

  1. customReaction
  2. customwas then quenched with water
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customto afford crude product, which
  7. customon purification by column chromatography

Sources & evidence

ORD record
ord-6c3822dff14744c8af4d2fbfc545ec6d
Source dataset
uspto-grants-2013_05
Patent number
US08440830B2

Reaction notes

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