Ethyl bromoacetate → HCID 69010851, compound

HRID 1376108Notes

Reaction equation

HRID 1376108 reaction equation
[NH2:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH3:13])=[CH:6][C:3]=1[C:4]#[N:5].C(=O)(O)[O-].[Na+].Br[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22]>C(O)C.[I-].[Na+]>[CH2:24]([O:23][C:21](=[O:22])[CH2:20][NH:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH3:13])=[CH:6][C:3]=1[C:4]#[N:5])[CH3:25]

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 516892Sodium BicarbonateHCID 7359672-Amino-4,5-dimethoxybenzonitrile

Product 1

HCID 69010851HCID 69010851, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 5238Sodium IodideCatalystHCID 702EthanolSolvent

Procedure

Under N2 suspend 2-amino-4,5-dimethoxybenzonitrile (2.0 g, 12.25 mmol) in ethanol (50 mL), and add sodium bicarbonate (3.09 g, 36.78 mmol) in one portion. By syringe, slowly add ethyl bromoacetate (2.72 mL, 24.5 mmol), and then sodium iodide (10 mg). Heat the reaction at 65° C. and then cool to ambient temperature. Filter the resulting solid and wash with ethyl acetate to dissolve the organics. Concentrate the filtrate to obtain 0.66 g (23%) of the title compound; MS 265(M+H).

Workup

  1. temperatureHeat
  2. customthe reaction at 65° C.
  3. filtrationFilter the resulting solid
  4. washwash with ethyl acetate
  5. dissolutionto dissolve the organics
  6. concentrationConcentrate the filtrate

Sources & evidence

ORD record
ord-3c0cf2c52d1440b38ef3bb0a15b71d85
Source dataset
uspto-grants-2007_01
Patent number
US07169925B2

Reaction notes

Loading…