Dichloromethane → 5-Chloro-1,3-dihydrobenzo[de]isochromene-6-carbonitrile

HRID 217287Notes

Reaction equation

N(OC(C)(C)C)=O.N[C:9]1[C:10]([C:22]#[N:23])=[C:11]2[CH:20]=[CH:19][CH:18]=[C:17]3[C:12]2=[C:13]([CH:21]=1)[CH2:14][O:15][CH2:16]3.C(Cl)[Cl:25]>C(#N)C.[Cu](Cl)Cl>[Cl:25][C:9]1[C:10]([C:22]#[N:23])=[C:11]2[CH:20]=[CH:19][CH:18]=[C:17]3[C:12]2=[C:13]([CH:21]=1)[CH2:14][O:15][CH2:16]3

Participants

Conditions

Temperature: 65 °C

Procedure

tert-Butyl nitrite (27.5 ml, 208 mmol) was added to a suspension of copper (II) chloride (22.5 g, 167 mmol) in anhydrous acetonitrile (500 mL) at room temperature under nitrogen atmosphere. The resulting dark green suspension was heated to the internal temperature of 65° C., and a solution of 5-amino-6-cyano-1H,3H benzo[de]isochromene (29.2 g, 139 mmol) in anhydrous acetonitrile (1000 mL) was added thereto. The reaction solution was stirred at 65° C. for 30 minutes, and then allowed to return to room temperature. The reaction solution was diluted with methylene chloride. The mixture was washed in succession with 1N aqueous hydrochloric acid solution and brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting crude product was purified by silica gel column chromatography using methylene chloride, and dried under reduced pressure. The title compound was obtained as yellow solid material (27.7 g, 87%).

Workup

customto return to room temperature
washThe mixture was washed in succession with 1N aqueous hydrochloric acid solution and brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe resulting crude product was purified by silica gel column chromatography
customdried under reduced pressure

Sources & evidence

ORD record: ord-76146e7c3adf4bb29e8233f7bd4ea205
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08193351B2

Reaction notes

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