Formic Acid → HCID 20280077, compound

HRID 1247925Notes

Reaction equation

HRID 1247925 reaction equation
[CH:1]([OH:3])=[O:2].C(O[C:8](=[O:10])C)(=O)C.O[CH2:12][CH2:13][NH:14][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1>O1CCCC1>[CH:1]([O:3][CH2:12][CH2:13][N:14]([C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)[CH:8]=[O:10])=[O:2]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 20280073HCID 20280073, compound

Product 1

HCID 20280077HCID 20280077, compoundYield 91.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of formic acid (5.02 g) and acetic anhydride (11.14 g) was stirred for 30 minutes at 40° to 45° C. and cooled in an ice bath. To the cold mixed anhydride was added a solution of 3-(2-hydroxyethyl)aminopyridine (5.80 g) in tetrahydrofuran (20 ml) under cooling in an ice bath and stirring, which was continued for two hours at room temperature. The mixture was evaporated to remove tetrahydrofuran and poured into water (100 ml). The mixture was adjusted to pH 6 to 7 with sodium bicarbonate and extracted with methylene chloride. The extract was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and evaporated to give 3-[N-(2-formyloxyethyl)formamido]-pyridine (7.47 g) as an oil.

Workup

  1. temperaturecooled in an ice bath
  2. temperatureunder cooling in an ice bath
  3. stirringstirring
  4. waitwhich was continued for two hours at room temperature
  5. customThe mixture was evaporated
  6. customto remove tetrahydrofuran
  7. additionpoured into water (100 ml)
  8. extractionextracted with methylene chloride
  9. washThe extract was washed with a saturated aqueous solution of sodium chloride
  10. dry with materialdried over magnesium sulfate
  11. customevaporated

Sources & evidence

ORD record
ord-69f46a3271074eda82d3e10f4b4deba0
Source dataset
uspto-grants-1985_06
Patent number
US04521413

Reaction notes

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