Sodium ethoxide → HCID 178515637, compound

HRID 707214Notes

Reaction equation

HRID 707214 reaction equation
[NH2:1][C:2]1[C:7](/[CH:8]=[CH:9]/[C:10]([O:12]C)=O)=[CH:6][CH:5]=[CH:4][N:3]=1.[O-]CC.[Na+]>C(O)C>[N:1]1[C:2]2[C:7](=[CH:6][CH:5]=[CH:4][N:3]=2)[CH:8]=[CH:9][C:10]=1[OH:12]

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 46318116(E)-Methyl 3-(2-aminopyridin-3-yl)acrylate

Product 1

HCID 178515637HCID 178515637, compoundYield 97.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(E)-Methyl 3-(2-aminopyridin-3-yl)acrylate (3.50 g, 19.64 mmol) was dissolved in ethanol (80 mL) and treated with sodium ethoxide (21 wt. % solution in denatured ethanol, ml, 26.8 mmol). The solution was heated at reflux for 2 hours then evaporated to dryness under reduced pressure. Saturated ammonium chloride (100 mL) and water (100 mL) were added to the crude and it was stirred for 10 minutes. The solid product was filtered off and dried by toluene azeotrope to give 1,8-naphthyridin-2-ol (2.80 g, 19.16 mmol, 83% yield) as a white powder.

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 2 hours
  3. customthen evaporated to dryness under reduced pressure
  4. additionSaturated ammonium chloride (100 mL) and water (100 mL) were added to the crude and it
  5. filtrationThe solid product was filtered off
  6. dry with materialdried by toluene azeotrope

Sources & evidence

ORD record
ord-e5f2015a894d4df99fe4c940c258fdd5
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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