Malononitrile → Naphthalene

HRID 431439Notes

Reaction equation

HRID 431439 reaction equation
OCC[C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[C:10](NC)=[C:9](C(=O)C)[CH:8]=[CH:7]2.C(#N)CC#N>N1C=CC=CC=1>[CH:10]1[C:11]2[C:6](=[CH:5][CH:4]=[CH:13][CH:12]=2)[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 8010MalononitrileHCID 69264593HCID 69264593, compound

Product 1

HCID 931Naphthalene

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of 201 mg (0.83 mmol) of 1-(6-2-hydroxyethyl-methylamino-2-naphthyl)-1-ethanone in pyridine (6 mL), malononitrile (236 mg, 3.6 mmol) was added and the mixture was heated at 95° C. for 24 hours. The solvent was removed in vacuo, and the residue was chromatographed by radial chromatography (4 mm SiO2 1% MeOH/CH2Cl2) to give 150 mg (73%) of 2-(1,1-dicyanopropen-2-yl)-6-2-hydroxyethyl)-methyl-amino)-naphthalene.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was chromatographed by radial chromatography (4 mm SiO2 1% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-f01c3331a5a54b53864be3346f30206c
Source dataset
uspto-grants-2003_12
Patent number
US06660530B2

Reaction notes

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