2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 68708930, compound

HRID 222094Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[C:17]2[CH2:16][CH2:15][C:14]3[C:10](=[CH:11][N:12](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:13]=3)[C:9]=2[N:8]([CH3:37])[C:7]=1[C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])=[O:5])[CH3:2].C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>O1CCOCC1>[CH2:1]([O:3][C:4]([C:6]1[C:17]2[C:9](=[C:10]3[C:14](=[CH:15][CH:16]=2)[NH:13][N:12]=[CH:11]3)[N:8]([CH3:37])[C:7]=1[C:38]([O:40][C:41]([CH3:42])([CH3:44])[CH3:43])=[O:39])=[O:5])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 1-methyl-7-trityl-1,4,5,7-tetrahydro-1,6,7-triaza-as -indacene-2,3-dicarboxylic acid 2-tert-butyl ester 3-ethyl ester VI (1.05 mmol) in 20 mL of dry dioxane under argon, DDQ (1.26 mmol) was added. The dark solution was heated at 100° C. for 4 h then the solvent was evaporated. The residue was dissolved in DCM, washed with water and with 20% aq sodium carbonate. The organic layers were dried (Na2SO4) and evaporated to dryness. The residue was purified by chromatography on silica gel (eluant: hexane/AcOEt 7:3) affording the title compound in 66% yield. ESI (+) MS: m/z 344 (MH+). 1H NMR: 1.34 (t, J=7.09, 3H), 1.59 (s, 9H), 4.12 (s, 3H), 4.33 (q, J=7.09, 2H), 7.44 (d, J=9.02, 1H), 7.90 (d, J=9.02, 1H), 8.47 (s, 1H), 13.43 (bs, 1H).

Workup

customthe solvent was evaporated
dissolutionThe residue was dissolved in DCM
washwashed with water and with 20% aq sodium carbonate
dry with materialThe organic layers were dried (Na2SO4)
customevaporated to dryness
customThe residue was purified by chromatography on silica gel (eluant: hexane/AcOEt 7:3)

Sources & evidence

ORD record: ord-97ba52104ed0436a88c703d73b590f6b
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08207180B2

Reaction notes

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