2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 11687512, compound

HRID 1357466Notes

Reaction equation

HRID 1357466 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH2:10][CH2:9][C:8](=[O:11])[NH:7][C:6]=1[C:12](=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:4].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1(C)C=CC=CC=1>[CH3:13][CH2:12][CH2:6][CH:5]([CH3:10])[CH3:3].[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8](=[O:11])[NH:7][C:6]=1[C:12](=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:4]

Participants

5

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinone2×HCID 67486064HCID 67486064, compound

Product 2

HCID 78922-MethylpentaneHCID 11687512HCID 11687512, compoundYield 69.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-Benzoyl-6-oxo-1,4,5,6-tetrahydropyridine-3-carboxylic acid methyl ester (5.97 g) and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ, 7.85 g) were stirred together at reflux in toluene (125 ml) for 24 h. More DDQ (7.85 g) was added and the mixture was stirred as before for a further 24 h. The solvent was removed in vacuo, and the residue was purified by flash chromatography on silica gel, eluting with 1:1 ethyl acetate:isohexane, yielding 2-benzoyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid methyl ester as a brown solid (2.07 g). 1H NMR (400 MHz, CDCl3) δ3.54 (3H, s), 6.60 (1H, d, J=9.7 Hz), 7.50 (2H, t, J=7.8 Hz), 7.64 (1H, t, J=7.4 Hz), 7.82 (2H, d, J=8.2 Hz), 7.95 (1H, d, J=9.7 Hz), 11.00 (1H, br s); MS (ES+) m/e 258 [MH]+, 226 [M−OMe]+.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by flash chromatography on silica gel
  3. washeluting with 1:1 ethyl acetate

Sources & evidence

ORD record
ord-ba813a78ada94e2e99661f59daad4489
Source dataset
uspto-grants-2003_07
Patent number
US06593325B1

Reaction notes

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