Acetic Acid → HCID 67791408, compound

HRID 653836Notes

Reaction equation

HRID 653836 reaction equation
O=[C:2]([C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=1)[CH2:3][C:4]#[N:5].Cl.[CH3:17][NH2:18].C([O-])(=O)C.[Na+].C(O)(=O)C>C1(C)C=CC=CC=1.C(OCC)(=O)C.Cl>[CH3:17][NH:18][C:2]([C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=1)=[CH:3][C:4]#[N:5]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 222856beta-Oxo-2-naphthalenepropanenitrileHCID 517045Sodium AcetateHCID 6364545Methylamine hydrochloride

Product 1

HCID 67791408HCID 67791408, compoundYield 58%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of β-oxo-2-naphthalenepropionitrile (5.0 g, 0.0256 mol) in toluene is treated with methylamine hydrochloride ()2.6 g, 0.0384 mol), sodium acetate (3.15 g, 0.0386 mol) and a catalytic amount of acetic acid, heated at reflux temperature (fitted with a Dean Stark trap) for 6 hours, cooled, diluted with ethyl acetate and dilute hydrochloric acid. The organic phase is dried over Na2SO4 and concentrated in vacuo to give a residue which is triturated under hexanes to give the title compound as a yellow solid, 3.1 g (58% yield) mp 138° C., identified by IR, 1NHMR and mass spectral analyses.

Workup

  1. temperatureat reflux temperature (
  2. customfitted with a Dean Stark trap) for 6 hours
  3. temperaturecooled
  4. dry with materialThe organic phase is dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customto give a residue which
  7. customis triturated under hexanes

Sources & evidence

ORD record
ord-d94f2da5002f430b99c1aeca0fbae274
Source dataset
uspto-grants-1992_07
Patent number
US05128485

Reaction notes

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