2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 67163785, compound

HRID 12211Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH2:9][N:8]([C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:16])[CH2:7][CH2:6][C:5]2=1.C(C1C(=O)C(Cl)=C(Cl)C(=[O:28])C=1C#N)#N.C1COCC1.O>C1COCC1>[C:15]([N:8]1[CH2:7][C:6](=[O:28])[C:5]2[C:4]3[C:12](=[CH:13][CH:14]=[C:2]([Cl:1])[CH:3]=3)[NH:11][C:10]=2[CH2:9]1)(=[O:16])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

Conditions

Temperature: -78 °C

Procedure

(6-chloro-1,3,4,9-tetrahydro-β-carbolin-2-yl)-phenyl-methanone (1.76 g, 5.66 mmol, 1 equiv.) and DDQ (2.31 g, 10.2 mmol, 1.8 equiv.) were mixed as solids and cooled to −78° C. 15 ml of a 9:1 THF/H2O solution was cooled to −78° C. and the resulting slurry was added to the cooled solids followed by an additional 15 ml of THF (also cooled to −78° C.). The deep blue solution was stirred at −78° C. for 2 hours and then gradually warmed to room temperature and stirred an additional two hours. The reaction was quenched by the addition of 1 N NaOH, and extracted with 3×150 ml EtOAc. The combined organic layers were washed with 2×100 ml 1 N HCl, 1×100 ml brine, dried over MgSO4, filtered and concentrated to yield 1.38 g (75%) of 2-benzoyl-6-chloro-1,2,3,9-tetrahydro-β-carbolin-4-one as oily orange solids.

Workup

additionthe resulting slurry was added to the cooled solids
temperaturealso cooled to −78° C.)
temperaturegradually warmed to room temperature
stirringstirred an additional two hours
customThe reaction was quenched by the addition of 1 N NaOH
extractionextracted with 3×150 ml EtOAc
washThe combined organic layers were washed with 2×100 ml 1 N HCl, 1×100 ml brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-a9c8b2ef391f41859897bec5f3ce5352
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07727985B2

Reaction notes

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