Water → HCID 14155946, compound

HRID 1253017Notes

Reaction equation

HRID 1253017 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][C:6]1[C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=[CH:8][N:7]=1)[CH3:2].C(=O)(O)[O-].[Na+].[CH2:21](I)[CH3:22].O>CN(C)C=O>[CH2:1]([O:3][C:4](=[O:15])[CH2:5][C:6]1[C:11]([C:12]([O:14][CH2:21][CH3:22])=[O:13])=[CH:10][CH:9]=[CH:8][N:7]=1)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 516892Sodium BicarbonateHCID 27637332-(2-ethoxy-2-oxoethyl)nicotinic acid

Product 1

HCID 14155946HCID 14155946, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of 54 g (0.26 mole) of 3-carboxy-2-pyridineacetic acid ethyl ester* and 24.4 g (0.29 mole) of sodium bicarbonate in 300 ml of dimethylformamide was added 60.8 g (0.39 mole) of ethyliodide. The mixture was stirred at 50° C. for 24 hr; cooled to 25° C. and treated with 300 ml of water. The aqueous solution was extracted 3 times with isopropyl ether. The isopropyl ether solution was extracted with dilute hydrochloric acid. The acid layer was made basic with sodium hydroxide and extracted with isopropyl ether. The ether layer was dried over anhydrous sodium sulfate, concentrated and the residue was distilled to give 47 g (76%), b.p. 128°-130° C./0.5 mm.

Workup

  1. temperaturecooled to 25° C.
  2. extractionThe aqueous solution was extracted 3 times with isopropyl ether
  3. extractionThe isopropyl ether solution was extracted with dilute hydrochloric acid
  4. extractionextracted with isopropyl ether
  5. dry with materialThe ether layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. distillationthe residue was distilled
  8. customto give 47 g (76%), b.p. 128°-130° C./0.5 mm

Sources & evidence

ORD record
ord-b0ddac46811b46028653a9d8fd972d53
Source dataset
uspto-grants-1988_05
Patent number
US04746657

Reaction notes

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