Ethyl bromoacetate → HCID 9267926, compound

HRID 556470Notes

Reaction equation

HRID 556470 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6].Br[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].C(N(CC)CC)C>ClCCl>[CH2:15]([O:14][C:12](=[O:13])[CH2:11][NH:6][C:5]1[CH:7]=[CH:8][CH:9]=[C:3]([O:2][CH3:1])[CH:4]=1)[CH3:16]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 8471TriethylamineHCID 108243-Methoxyaniline

Product 1

HCID 9267926HCID 9267926, compoundYield 27.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The mixture of 3-methoxyaniline (3.7 g), ethyl bromoacetate (5 g) and triethylamine (4 g) in dichloromethane (30 mL) was stirred at room temperature for overnight. The mixture was washed with water (50 ml), dried over Na2SO4 and concentrated. The residue was purified with chromatography to give 1.7 g of (3-methoxy-phenylamino)-acetic acid ethyl ester. 1HNMR: δ 1.33 (3H), 3.796 (3H), 3.92 (2H), 4.26 (2H), 6.21 (1H), 6.29 (1H), 6.36 (1H), 7.13 (1H).

Workup

  1. washThe mixture was washed with water (50 ml)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified with chromatography

Sources & evidence

ORD record
ord-0caadcf0a6af4cf6b2dfa6f68695b6ad
Source dataset
uspto-grants-2011_11
Patent number
US08058269B2

Reaction notes

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