Hydrochloric Acid → (6-ethoxypyridin-3-yl)methylamine

HRID 2041511Notes

Reaction equation

HRID 2041511 reaction equation
[CH2:1]([O:3][C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][N:5]=1)[CH3:2].Cl>C1COCC1>[NH2:9][CH2:8][C:7]1[CH:10]=[CH:11][C:4]([O:3][CH2:1][CH3:2])=[N:5][CH:6]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 189294456-Ethoxypyridine-3-carbonitrile

Product 1

HCID 16784151(6-ethoxypyridin-3-yl)methylamineYield 40%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Add a solution of 1M BH3-THF complex in THF (7 mL, 7 mmol) to a solution of 6-(ethoxy)nicotinonitrile (911 mg, 4.41 mmol) in anhydrous THF (7 mL) and stir the mixture overnight at reflux. Add a second aliquot of 1M BH3-THF complex in THF (7 mL, 7 mmol) and stir the mixture overnight at reflux. Add 5N aqueous HCl (10 mL) cautiously and stir the mixture overnight at room temperature. Concentrate in vacuo then dissolve the crude mixture in methanol and filter through an SCX column eluting with methanol followed by 3M ammonia in methanol to obtain the title compound (250 mg, 40%). MS (ES+) m/z: 153 (M+H)+.

Workup

  1. temperatureat reflux
  2. stirringstir the mixture overnight
  3. temperatureat reflux
  4. stirringstir the mixture overnight at room temperature
  5. concentrationConcentrate in vacuo
  6. dissolutionthen dissolve the crude mixture in methanol
  7. filtrationfilter through an SCX column
  8. washeluting with methanol

Sources & evidence

ORD record
ord-bb65a23cfe424a67a4dfe2b72fd1f980
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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