Acetic Acid → HCID 14372174, compound

HRID 1383018Notes

Reaction equation

HRID 1383018 reaction equation
[CH2:1]([N:3]([CH2:15][CH3:16])[C:4]([C:6]1[CH:7]=[C:8]2[CH:14]=[CH:13][O:12][C:9]2=[N:10][CH:11]=1)=O)[CH3:2].B.C(O)(=O)C.Cl>O1CCCC1>[CH2:1]([N:3]([CH2:4][C:6]1[CH:7]=[C:8]2[CH:14]=[CH:13][O:12][C:9]2=[N:10][CH:11]=1)[CH2:15][CH3:16])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 6331BoraneHCID 14372173HCID 14372173, compound

Product 1

HCID 14372174HCID 14372174, compoundYield 77.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of N,N-diethyl furo[2,3-b]pyridine-5-carboxamide (3.6 g, 16.5 mmol) in dry tetrahydrofuran (35 mL), under a nitrogen atmosphere, was added 1M borane in THF (52 mL, 52 mmol). This solution was warmed at 60° C. for 2-3 hours and then glacial acetic acid (3 mL, 52 mmol) was carefully added. After 0.5 hours, dilute hydrochloric acid (10%) was added to the reaction and the aqueous layer was separated and made basic with sodium hydroxide solution. The product was extracted into methylene chloride, dried over anhydrous sodium sulfate, filtered through a pad of charcoal and the solvent evaporated to give crude oily product (2.6 g). This material was distilled under vacuum to give purified produt (1.2 g, 36% yield), bp: 120°-121° C./1.5 mmHg. A small portion was treated with ethanolic hydrogen chloride to give the hydrochloride salt which was recrystallized from isopropanol, mp: 206°-208° C.

Workup

  1. customthe aqueous layer was separated
  2. extractionThe product was extracted into methylene chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered through a pad of charcoal
  5. customthe solvent evaporated

Sources & evidence

ORD record
ord-971a2feb944846759890d7610f939c74
Source dataset
uspto-grants-1989_02
Patent number
US04808595

Reaction notes

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