Acetyl chloride → 2-Acetamido-6-aminopyridine

HRID 1716904

Reaction equation

HRID 1716904 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH2:8])[N:3]=1.[C:9](Cl)(=[O:11])[CH3:10]>O1CCOCC1>[NH2:8][C:4]1[N:3]=[C:2]([NH:1][C:9](=[O:11])[CH3:10])[CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 88612,6-Diaminopyridine

Product 1

HCID 37673452-Acetamido-6-aminopyridineYield 76.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve 2,6-diaminopyridine (9.822 g, 90 mmol) in dioxane (100 mL) and cool to 0° C. Add acetyl chloride (2.355 g, 2.1 mL, 30 mmol) slowly and stir for 1 hr. at 0° C. Remove the ice bath and stir at room temperature overnight. Quench the reaction mixture with saturated NaHCO3 solution, extract with ethyl acetate three times. Combine the organic layers, dry over Na2SO4, filter, and concentrate to give a solid. Chromatography on silica gel, eluting with a gradient of 60-70% ethylacetate in hexanes affords the title intermediate (3.45 g, 76%): mass spectrum (ion spray): m/z=152.1 (M+1); 1H NMR (CDCl3, ppm): 7.49 (m, 3H), 6.28 (d, 1H), 4.31 (s, br, 2H), 2.19 (s, 3H).

Workup

  1. customat 0° C
  2. customRemove the ice bath
  3. customQuench the reaction mixture with saturated NaHCO3 solution
  4. extractionextract with ethyl acetate three times
  5. dry with materialCombine the organic layers, dry over Na2SO4
  6. filtrationfilter
  7. concentrationconcentrate
  8. customto give a solid
  9. washChromatography on silica gel, eluting with a gradient of 60-70% ethylacetate in hexanes

Sources & evidence

ORD record
ord-cbc107f8ed8c4b09a436742786952ccd
Source dataset
uspto-grants-2010_09
Patent number
US07803813B2

Linked notes

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