Ethylenediaminetetraacetic Acid → HCID 12263327, compound

HRID 1818891Notes

Reaction equation

Cl[C:2]1[N:9]=[C:8]([CH3:10])[CH:7]=[C:6]([CH3:11])[C:3]=1[C:4]#[N:5].[Cl-].C[Zn+].[CH2:15](N(CC(O)=O)CC(O)=O)CN(CC(O)=O)CC(O)=O.C(=O)([O-])[O-].[K+].[K+]>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:15][C:2]1[N:9]=[C:8]([CH3:10])[CH:7]=[C:6]([CH3:11])[C:3]=1[C:4]#[N:5]

Participants

Conditions

Temperature: 0 °C

Procedure

2-chloro-4,6-dimethyl-nicotinonitrile (700 mg, 4.201 mmol) and Pd(PPh3)4 (243 mg, 0.210 mmol) were dissolved in 20 mL of anhydrous THF, added with methylzinc chloride (2M CH3ZnCl/THF, 12.6 mL, 25.21 mmol) and refluxed for about 40 hours under the nitrogen atmosphere. The mixture was added to a saturated EDTA solution (50 mL), and neutralized with potassium carbonate while stirring at 0° C. and then extracted twice with 150 mL of methylene chloride. The resulting organic layer was dried using anhydrous sodium sulfate, filtered and concentrated. A silica gel column chromatography (25% EtOAc/Hexanes) was performed on the resulting residue and 535 mg (87%) of 2,4,6-trimethyl-nicotinonitrile was obtained in white solid.

Workup

temperaturerefluxed for about 40 hours under the nitrogen atmosphere
extractionextracted twice with 150 mL of methylene chloride
customThe resulting organic layer was dried
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-44024406b3744b60aaeb195406c0b6a1
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07601736B2

Reaction notes

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