4,4-Diethoxybutanenitrile → HCID 178467804, compound

HRID 1787826Notes

Reaction equation

HRID 1787826 reaction equation
[CH2:1]([O:3][CH:4]([O:9][CH2:10][CH3:11])[CH2:5][CH2:6][C:7]#[N:8])[CH3:2].Cl.[NH2:13][OH:14].C(=O)(O)[O-].[Na+]>CO>[CH2:10]([O:9][CH:4]([O:3][CH2:1][CH3:2])[CH2:5][CH2:6][C:7](=[NH:8])[NH:13][OH:14])[CH3:11]

Participants

5

Reactant 3

HCID 876164,4-DiethoxybutanenitrileHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 178467804HCID 178467804, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4,4-diethoxybutanenitrile (5.0 g, 32 mmol), hydroxylamine hydrochloride (2.4 g, 35 mmol) and sodium bicarbonate (2.9 g, 35 mmol) in methanol (50 mL) was refluxed for 5 hours. After cooling to room temperature, the reaction mixture was concentrated and the residue was diluted with EtOAc and water. The water layer was extracted with EtOAc (2×). The combined organic layers were washed with water, dried over Na2SO4, filtered and concentrated to give the product, which was used next step without purification. 1HNMR (300 MHz, CD3Cl): δ 4.73 (br, 1H), 4.51 (t, J=5.5 Hz, 1H), 3.66 (m, 2H), 3.50 (m, 2H), 2.21 (t, J=8.2 Hz, 2H), 1.86 9m, 2H), 1.19 (t, J=8.2 Hz, 6H).

Workup

  1. temperaturewas refluxed for 5 hours
  2. concentrationthe reaction mixture was concentrated
  3. additionthe residue was diluted with EtOAc and water
  4. extractionThe water layer was extracted with EtOAc (2×)
  5. washThe combined organic layers were washed with water
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give the product, which
  10. customwithout purification

Sources & evidence

ORD record
ord-a302dec015f0498c9b6d3a146f377c91
Source dataset
uspto-grants-2009_03
Patent number
US07511050B2

Reaction notes

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