Water → 6-[2-Nitro-4-(trifluoromethyl)phenoxy]quinoline-2-carbonitrile

HRID 446193Notes

Reaction equation

[C:1]([C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([OH:13])[CH:9]=2)[N:4]=1)#[N:2].[Cl-].[N+:15]([C:18]1[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[CH:20][CH:19]=1)([O-:17])=[O:16].C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O.C(Cl)Cl>[C:1]([C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:13][C:19]3[CH:20]=[CH:21][C:22]([C:24]([F:27])([F:25])[F:26])=[CH:23][C:18]=3[N+:15]([O-:17])=[O:16])[CH:9]=2)[N:4]=1)#[N:2]

Participants

Conditions

Temperature: 100 °C

Procedure

The mixture of 2-cyano-6-hydroxyquinoline (0.50 g, 2.94 mmol), 2-nitro-4-trifluoromethylbenzene chloride (0.67 g, 2.94 mmol) and potassium carbonate (0.41 g, 2.97 mmol) in 30 ml of DMSO was heated to 100° C. for 30 min. Upon cooling to room temperature, the mixture was poured into 30 ml of cold water and exacted three times with methylene chloride. The combined organic layer was washed with water and dried over magnesium sulfate. The product was purified by flash chromatography using heptane/methylene chloride (1:2) as eluent in a yield of 35%.

Workup

temperatureUpon cooling to room temperature
washThe combined organic layer was washed with water
dry with materialdried over magnesium sulfate
customThe product was purified by flash chromatography

Sources & evidence

ORD record: ord-72f8c18f7b4848229b893b2263e6f56f
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08476450B2

Reaction notes

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