Ethanol → Ethyl 2-aminopyridine-3-carboxylate

HRID 2392707Notes

Reaction equation

HRID 2392707 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].OS(O)(=O)=O.C([O-])([O-])=O.[Na+].[Na+].[CH2:22](O)[CH3:23]>>[NH2:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH2:22][CH3:23])=[O:5]

Participants

5

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 729302-Aminonicotinic acid

Product 1

HCID 12433260Ethyl 2-aminopyridine-3-carboxylateYield 60%

Conditions

Temperature
120 °C

Procedure

Absolute ethanol (10 mL) was added to 2-aminonicotinic acid (120, commercially available) (3.9 g, 28 mmol). To the resulting stirred mixture was added H2SO4 (96%, 5 mL). The mixture was heated and refluxed at 120° C. for ~4 h. The suspension was cooled to room temperature, poured over ice (30 g), and neutralized to pH 5 using solid Na2CO3. The aqueous suspension was extracted with EtOAc (3×25 mL). These combined organic extracts were washed with water (3×30 mL), dried (Na2SO4), and rota-evaporated to dryness, leaving the title compound as off-white crystals (2.8 g, 60%); mp 90.5°-92.5° C. (Lit., 94°-95° C., Hirai, E., Chem. Pharm. Bull. 14:861 (1966)). 1H NMR (CDCl3): δ1.38 (t, J=7.2, 3, CH3CH2), 4.34 (q, J=7.2, 2, CH3CH2O), 6.40 (bm, 2, NH2), 6.62 (dd, J1 =4.9, J2 =7.8, 1, H-4), 8.14 (dd, J1 =1.0, J2 =8.4, 1, H-5), 8.21 (dd, J1 =1.2, J2 =3.8, 1, H-6).

Workup

  1. temperatureThe mixture was heated
  2. temperatureThe suspension was cooled to room temperature
  3. extractionThe aqueous suspension was extracted with EtOAc (3×25 mL)
  4. washThese combined organic extracts were washed with water (3×30 mL)
  5. dry with materialdried (Na2SO4)
  6. customrota-evaporated to dryness

Sources & evidence

ORD record
ord-18d95160b7284c0c9c9d70109fadf9f0
Source dataset
uspto-grants-1998_09
Patent number
US05801183

Reaction notes

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