2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 2-Cyano-3,4-dimethyl-5-nitropyridine

HRID 723720Notes

Reaction equation

[C:1]([C:3]1[C:8]([CH3:9])=[CH:7][C:6]([N+:10]([O-:12])=[O:11])=[CH:5][N:4]=1)#[N:2].[CH3:13][Mg]Br.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C1COCC1>[C:1]([C:3]1[C:8]([CH3:9])=[C:7]([CH3:13])[C:6]([N+:10]([O-:12])=[O:11])=[CH:5][N:4]=1)#[N:2]

Participants

Conditions

Temperature: -70 °C

Procedure

2-Cyano-3-methyl-5-nitropyridine (0.33g, 2 mmol) was dissolved in 10 mL of THF and cooled in a dry ice/acetone bath under nitrogen. Methylmagnesium bromide (1.33 mL, 4 mmol) was added via syringe over five mins. The reaction was stirred for 2 h at −70° C. DDQ (0.068g, 3 mmol) in 7 mL of THF was added and the mixture warmed to 25° C. The solvent was removed in vacuo and the residue was purified by silica gel chomatography using CH2Cl2 as the eluent to give compound 773A (0.15g, 42%) as a red oil.

Workup

temperaturecooled in a dry ice/acetone bath under nitrogen
temperaturethe mixture warmed to 25° C
customThe solvent was removed in vacuo
customthe residue was purified by silica gel chomatography

Sources & evidence

ORD record: ord-3fb4bea0f53d44c4a058ee27d00617d4
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07141578B2

Reaction notes

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