Acetonitrile → 3-(6-Methoxy-naphthalen-2-yl)-3-oxo-propionitrile

HRID 1695219Notes

Reaction equation

HRID 1695219 reaction equation
CO[C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:15][CH3:16])[CH:11]=2)[CH:6]=1)=[O:4].[H-].[Na+].[C:19](#[N:21])[CH3:20]>C1(C)C=CC=CC=1>[CH3:16][O:15][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[CH:6]=[C:5]([C:3](=[O:4])[CH2:20][C:19]#[N:21])[CH:14]=[CH:13]2

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 24758Sodium hydrideHCID 604020Methyl 6-methoxy-2-naphthoate

Product 1

HCID 671886013-(6-Methoxy-naphthalen-2-yl)-3-oxo-propionitrile

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 6-methoxy-naphthalene-2-carboxylic acid methyl ester (1.0 g, 4.7 mmol) in dry toluene (8 mL), NaH (0.55 mg, 9.4 mmol) were added and the mixture was heated at 90° C. To the hot solution, acetonitrile (1.2 mL) was added dropwise. The reaction was then heated for 18 hours and the product precipitated from the reaction mixture as its sodium salt.

Workup

  1. temperatureThe reaction was then heated for 18 hours
  2. customthe product precipitated from the reaction mixture as its sodium salt

Sources & evidence

ORD record
ord-fd27605a8f18448884a75736b5b66078
Source dataset
uspto-grants-2012_04
Patent number
US08163729B2

Reaction notes

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