Tetrahydrofuran → HCID 20280071, compound

HRID 1247926Notes

Reaction equation

HRID 1247926 reaction equation
C([O:3][CH2:4][CH2:5][N:6]([C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1)[CH:7]=[O:8])=O.C(=O)(O)[O-].[Na+].O1CCCC1>O>[OH:3][CH2:4][CH2:5][N:6]([C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1)[CH:7]=[O:8]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 20280077HCID 20280077, compound

Product 1

HCID 20280071HCID 20280071, compoundYield 76.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-[N-(2-formyloxyethyl)formamido]-pyridine (7.01 g) and sodium bicarbonate (3.04 g) in a mixed solution of tetrahydrofuran (60 ml) and water (110 ml) was stirred for 8 hours at 45° to 46° C. The reaction mixture was extracted with a mixed solvent of chloroform and ethanol (1:1) and the extract was evaporated. The residue was dissolved in a mixed solvent of chloroform and ethanol (4:1) and subjected to column chromatography on silica gel (150 g). The elution was carried out with the same solvent and the fractions containing an object compound were collected and evaporated to give 3-[N-(2-hydroxyethyl)formamido]pyridine (4.60 g) as an oil.

Workup

  1. extractionThe reaction mixture was extracted with a mixed solvent of chloroform and ethanol (1:1)
  2. customthe extract was evaporated
  3. dissolutionThe residue was dissolved in a mixed solvent of chloroform and ethanol (4:1)
  4. washThe elution
  5. additionthe fractions containing an object compound
  6. customwere collected
  7. customevaporated

Sources & evidence

ORD record
ord-1fddcb5cb1a748f2ae6b8d5fa9544842
Source dataset
uspto-grants-1985_06
Patent number
US04521413

Reaction notes

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