Hydrochloric Acid → (2-Amino-4-methoxyphenyl)(phenyl)methanone

HRID 1497262Notes

Reaction equation

[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:9][C:10]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:11]=1[C:12]#N.Cl.[OH-:21].[Na+]>C(OCC)C>[NH2:9][C:10]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:11]=1[C:12]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:21]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of phenylmagnesium bromide (6.75 ml, 3M solution in diethyl ether, 20.2 mmol) in diethyl ether (15 ml) was added dropwise to a solution of 2-amino-4-methoxybenzonitrile (1000 mg, 6.75 mmol) in diethyl ether (20 ml) at 0° C. The resulting suspension was heated to reflux for 2 h. The mixture was then cooled to 0° C. and 2N HCl (40 ml) was added very carefully. After complete addition, the mixture was heated to 55° C. for 2 h. Then 3N NaOH (˜20 ml) was added at 0° C. to adjust the pH to 9. The mixture was extracted with EtOAc and the combined organic extracts were washed with brine, dried with Na2SO4 and evaporated. The remaining residue was purified by column chromatography (silica gel, heptane/EtOAc 85:15-70:30) to afford the title compound (1300 mg, 85%) as yellow solid. MS (ESI): 228.4 (M+H)+.

Workup

temperatureThe resulting suspension was heated
temperatureto reflux for 2 h
additionAfter complete addition
temperaturethe mixture was heated to 55° C. for 2 h
extractionThe mixture was extracted with EtOAc
washthe combined organic extracts were washed with brine
dry with materialdried with Na2SO4
customevaporated
customThe remaining residue was purified by column chromatography (silica gel, heptane/EtOAc 85:15-70:30)

Sources & evidence

ORD record: ord-58c601a713444577a22c8962b6f28117
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199938B2

Reaction notes

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