Ammonium Acetate → 1-[8-(3-Fluorophenyl)-5-methylquinolin-7-yl]ethanamine

HRID 1192562Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]([C:19](=O)[CH3:20])=[CH:10][C:11]([CH3:18])=[C:12]3[C:17]=2[N:16]=[CH:15][CH:14]=[CH:13]3)[CH:5]=[CH:6][CH:7]=1.C([O-])(=O)C.[NH4+].C([BH3-])#[N:28].[Na+]>CO.C(#N)C>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]([CH:19]([NH2:28])[CH3:20])=[CH:10][C:11]([CH3:18])=[C:12]3[C:17]=2[N:16]=[CH:15][CH:14]=[CH:13]3)[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of 1-[8-(3-fluorophenyl)-5-methylquinolin-7-yl]ethanone (50 mg, 0.2 mmol) and ammonium acetate (138 mg, 1.79 mmol) in methanol (1.0 mL) and acetonitrile (1.0 mL) was heated at 65° C. in a sealed tube for 30 minutes. After cooling to room temperature, sodium cyanoborohydride (22.5 mg, 0.358 mmol). The reaction was heated at 65° C. for another 4 hours, then cooled to room temperature and quenched with sat. sodium bicarbonate, extracted with dichloromethane. The combined extracts were dried over magnesium sulfate and evaporated to dryness. The residue was used directly in the next step. LCMS calculated for C18H18FN2 (M+H)+: m/z=281.1; Found: 281.1.

Workup

temperatureAfter cooling to room temperature
temperatureThe reaction was heated at 65° C. for another 4 hours
temperaturecooled to room temperature
customquenched with sat. sodium bicarbonate
extractionextracted with dichloromethane
dry with materialThe combined extracts were dried over magnesium sulfate
customevaporated to dryness

Sources & evidence

ORD record: ord-df7050142b4740a19076534e87656050
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680108B2

Reaction notes

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