Methanol → 2-[(Cyanomethyl)aminomethylene]heptanonitrile

HRID 892472Notes

Reaction equation

HRID 892472 reaction equation
[CH:1]([CH:3]([CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[C:4]#[N:5])=O.C([O-])(=O)C.[Na+].Cl.[NH2:17][CH2:18][C:19]#[N:20].CO>CO.O.C(OCC)(=O)C.CCCCCC>[C:18]([CH2:19][NH:20][CH:1]=[C:3]([CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[C:4]#[N:5])#[N:17]

Participants

7

Reactant 4

HCID 887MethanolHCID 517045Sodium AcetateHCID 11491918Aminoacetonitrile hydrochlorideHCID 198955292-Formylheptanonitrile

Product 1

HCID 867443652-[(Cyanomethyl)aminomethylene]heptanonitrile

Reagents, catalysts & solvents 2

HCID 21226206Ethyl acetate hexaneSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

2-Formylheptanonitrile (10.7 g), sodium acetate (7.9 g) and aminoacetonitrile hydrochloride (8.9 g) were mixed together in 200 ml of methanol: water (8:2). After stirring for 2 hours at ambient temperature the methanol was removed under aspirator vacuum and the residue partitioned between ethyl acetate and water. The layers were separated and the ethyl acetate layer was washed with brine, dried (Na2SO4) and concentrated to leave a yellow oil. Chromatographic purification of the material over silica gel using ethyl acetate/hexane as the eluent afforded a light yellow solid as a mixture of isomers (11.6 g, 85%): tlc, Rf =0.37 and 0.50 silica gel, ethyl acetate:hexane (1:1).

Workup

  1. customwas removed under aspirator vacuum
  2. customthe residue partitioned between ethyl acetate and water
  3. customThe layers were separated
  4. washthe ethyl acetate layer was washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customto leave a yellow oil
  8. customChromatographic purification of the material over silica gel
  9. customafforded a light yellow solid
  10. additionas a mixture of isomers (11.6 g, 85%)

Sources & evidence

ORD record
ord-df0cb27fbf7c4d4184b79d1870f196cf
Source dataset
uspto-grants-1992_06
Patent number
US05118688

Reaction notes

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