Ethyl Acetate → [5-Acetyl-3-(tert-butyl)-2-methoxyanilino]methyl cyanide

HRID 1295970Notes

Reaction equation

Br[CH2:2][C:3]#[N:4].C(=O)([O-])[O-].[K+].[K+].[NH2:11][C:12]1[CH:13]=[C:14]([C:24](=[O:26])[CH3:25])[CH:15]=[C:16]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:17]=1[O:18][CH3:19].C(OCC)(=O)C>CN(C)C=O>[C:24]([C:14]1[CH:15]=[C:16]([C:20]([CH3:21])([CH3:22])[CH3:23])[C:17]([O:18][CH3:19])=[C:12]([CH:13]=1)[NH:11][CH2:2][C:3]#[N:4])(=[O:26])[CH3:25]

Participants

Conditions

Temperature: 70 °C

Procedure

Bromoacetonitrile (6 ml) and potassium carbonate (1.4 g) were added to a solution of 1-[3-amino-5-(tert-butyl)-4-methoxyphenyl]-1-ethanone (2.0 g, 9.0 mmol) in dimethylformamide (50 ml) and the mixture was stirred at 70° C. for 3 hours. The reaction mixture was cooled to room temperature, ethyl acetate was added, washed was performed with water and brine in that order, the organic layer was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (3.2 g) as a yellow oil.

Workup

temperatureThe reaction mixture was cooled to room temperature
washwashed
dry with materialthe organic layer was dried over anhydrous magnesium sulfate
distillationthe solvent was distilled off under reduced pressure
customThe residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

Sources & evidence

ORD record: ord-c8d4d4db58d648f1beba4163cba6303f
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07244730B2

Reaction notes

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