Bromine → HCID 66617942, compound

HRID 911071Notes

Reaction equation

HRID 911071 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:5]=[CH:4][N:3]=1.[Br:14]Br>C(O)(=O)C>[NH2:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:5]([Br:14])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 66617889945988-97-6

Product 1

HCID 66617942HCID 66617942, compoundYield 45.53%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A flask was charged with ethyl 2-(2-aminopyridin-4-yl)acetate (12.45 g, 69.09 mmol) and acetic acid (100 mL). Bromine (3.550 ml, 69.09 mmol) was added, and the reaction mixture was stirred for 3 hours. The solvent was evaporated in vacuo and the residue was mixed with ice, basified with ammonium hydroxide, and extracted with ethyl acetate. The combined organic layers were washed with brine and concentrated. The residual brown oil was purified by silica gel chromatography, eluting with 1-2% methanol/dichloromethane to provide the desired product (8.15 g, 45.53% yield) as pale yellow solid.

Workup

  1. customThe solvent was evaporated in vacuo
  2. additionthe residue was mixed with ice
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. concentrationconcentrated
  6. customThe residual brown oil was purified by silica gel chromatography
  7. washeluting with 1-2% methanol/dichloromethane

Sources & evidence

ORD record
ord-e39fa3e7cf3240da9cab8a2414608f32
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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