Ethanol → HCID 2823185, compound

HRID 1294064Notes

Reaction equation

HRID 1294064 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)C(O)=O.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:18])=CC=1.C([N:30]([CH2:33]C)CC)C.[CH2:35]([OH:37])[CH3:36]>>[Br:1][C:2]1[CH:10]=[C:6]([NH:30][C:33](=[O:18])[O:37][CH2:35][CH3:36])[CH:5]=[N:4][CH:3]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 887075-Bromonicotinic acidHCID 199401P,P-Diphenylphosphinic azide

Product 1

HCID 2823185HCID 2823185, compoundYield 19%

Procedure

To a solution of 5-bromonicotinic acid (20.0 g, 99.0 mmol) in ethanol (300 mL) was added DPPA (21.6 mL, 100.0 mmol) followed by triethylamine (14.3 mL, 103.0 mmol) then refluxed overnight. After cooling, a half amount of solvent was removed by evaporation. The ethanol solution was extracted with ethyl acetate. The organic layer was washed with NaHCO3 (aq) and brine, dried over Na2SO4 then evaporated. Sequence purification on SiO2 column chromatography gave the title compound (4.55 g, 19%): MS m/e 245, 246 (M+1).

Workup

  1. temperaturethen refluxed overnight
  2. temperatureAfter cooling
  3. customa half amount of solvent was removed by evaporation
  4. extractionThe ethanol solution was extracted with ethyl acetate
  5. washThe organic layer was washed with NaHCO3 (aq) and brine
  6. dry with materialdried over Na2SO4
  7. customthen evaporated
  8. customSequence purification on SiO2 column chromatography

Sources & evidence

ORD record
ord-aee01e85cbab4ff8a17eed60c3e55084
Source dataset
uspto-grants-2007_07
Patent number
US07238813B2

Reaction notes

Loading…