Sodium ethoxide → HCID 54710119, compound

HRID 902482Notes

Reaction equation

HRID 902482 reaction equation
[O-]CC.[Na+].CO[C:7]([C:9]1[S:10][CH:11]=[CH:12][C:13]=1[NH:14][C:15](=[O:22])[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[O:8]>C(O)C>[CH2:20]([O:19][C:17]([C:16]1[C:15](=[O:22])[NH:14][C:13]2[CH:12]=[CH:11][S:10][C:9]=2[C:7]=1[OH:8])=[O:18])[CH3:21]

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 2807589HCID 2807589, compound

Product 1

HCID 54710119HCID 54710119, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium ethoxide (0.67 g, 9.29 mmol) was added to a solution of 3-(2-ethoxycarbonyl-acetylamino)-thiophene-2-carboxylic acid methyl ester (1) (2.18 g, 7.74 mmol) in anhydrous ethanol and refluxed overnight. The solution was cooled and excess solvent was distilled off The residue was dissolved in water and acidified by cold diluted HCl solution. The solids formed were filtered, washed by water, and dried under vacuum at room temperature to yield 1.0 g (55%) of 7-hydroxy-5-oxo-4,5-dihydro-thieno[3,2-b]pyridine-6-carboxylic acid ethyl ester as white solid. MP 218° C.; 1H NMR (400 MHz, DMSO-d6) δ 1.28 (t, J=7.2 Hz, 3H), 4.29 (q, J=7.2 Hz, 2H), 6.96 (d, J=5.6 Hz, 1H), 8.07 (d, J=5.6 Hz, 1H) ppm; MS m/z=240 amu (M++1).

Workup

  1. temperaturerefluxed overnight
  2. temperatureThe solution was cooled
  3. distillationexcess solvent was distilled off The residue
  4. dissolutionwas dissolved in water
  5. customThe solids formed
  6. filtrationwere filtered
  7. washwashed by water
  8. customdried under vacuum at room temperature

Sources & evidence

ORD record
ord-aceb3aece9f0449bb7f5afea9f0bd064
Source dataset
uspto-grants-2008_04
Patent number
US07365200B2

Reaction notes

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