Bromide ion → HCID 16751620, compound

HRID 1394402Notes

Reaction equation

HRID 1394402 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N+:3]=1[CH2:9][C:10]([O:12]CC)=O.[Br-].C[O-].[Na+]>CO.O>[Br:8][C:5]1[CH:6]=[CH:7][C:2]2[N:3]([CH2:9][C:10](=[O:12])[N:1]=2)[CH:4]=1

Participants

6

Reactant 3

HCID 259Bromide ionHCID 4560212HCID 4560212, compoundHCID 10942334Sodium Methoxide

Product 1

HCID 16751620HCID 16751620, compoundYield 3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 2-Amino-5-bromo-1-ethoxycarbonylmethyl-pyridinium; bromide (2.86 g, 8.4 mmol) in methanol (30 mL) was added sodium methoxide (25 wt %, 2.5 mL, 10.1 mmol). The reaction mixture was stirred at room temperature overnight under argon. The reaction mixture was diluted with water and then extracted three times with ethyl acetate. The organic extracts were washed with brine, dried over magnesium sulfate, filtered, evaporated to yield a tan solid. The crude material was purified by column chromatography eluting with 3, 5, and 10% methanol/dichloromethane. The product was obtained as a brown solid (56 mg, 3%). 1H NMR (CDCl3) δ 7.85 (s, 1H), 7.67 (dd, J=1.6, 9.5 Hz, 1H), 7.07 (d, J=9.5 Hz, 1H), 4.52 (s, 2H); MS (m/e): 215 (MH+); HRMS: calc'd MH+ for C7H5BrN2O 212.9672; found 212.9664.

Workup

  1. extractionextracted three times with ethyl acetate
  2. washThe organic extracts were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customto yield a tan solid
  7. customThe crude material was purified by column chromatography
  8. washeluting with 3, 5, and 10% methanol/dichloromethane

Sources & evidence

ORD record
ord-6398843a20e44fb78b14978242e24dd4
Source dataset
uspto-grants-2008_03
Patent number
US07348432B2

Reaction notes

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