Acetyl chloride → 3-acetyl-2-methyl-1H-indole-5-carbonitrile

HRID 1015447Notes

Reaction equation

[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][C:7]([C:11]#[N:12])=[CH:6][CH:5]=2.[Sn](Cl)(Cl)(Cl)Cl.[C:18](Cl)(=[O:20])[CH3:19].[OH-].[Na+]>ClCCl>[C:18]([C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:11]#[N:12])[CH:8]=2)[NH:3][C:2]=1[CH3:1])(=[O:20])[CH3:19]

Participants

Conditions

Temperature: 0 °C

Procedure

A 500 mg portion of 2-methyl-1H-indole-5-carbonitrile was dissolved in 5 ml of dichloromethane, and 27.0 ml of 1 M tin tetrachloride (a dichloromethane solution) was added dropwise thereto at 0° C., followed by stirring at 0° C. for 10 minutes. Then, 0.27 ml of acetyl chloride was added thereto at 0° C., followed by overnight stirring at room temperature. A 25 ml portion of a 2 M sodium hydroxide aqueous solution was added thereto at 0° C. to adjust the pH to 12, followed by stirring at 0° C. for 1 hour and extraction with a 20% methanol-chloroform mixed solvent. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate, and then the solvent was evaporated under a reduced pressure to obtain 607 mg of 3-acetyl-2-methyl-1H-indole-5-carbonitrile as a beige solid.

Workup

customat 0° C.
waitat 0° C., followed by overnight
stirringstirring at room temperature
customat 0° C.
stirringby stirring at 0° C. for 1 hour
extractionextraction with a 20% methanol-chloroform mixed solvent
washThe organic layer was washed with saturated brine
dry with materialdried over anhydrous sodium sulfate
customthe solvent was evaporated under a reduced pressure

Sources & evidence

ORD record: ord-e7aafd31be08404782f238b42cfd94f4
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07985764B2

Reaction notes

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