Ammonium Acetate → 1-[5-Chloro-8-(3-fluorophenyl)quinolin-7-yl]ethanamine

HRID 1192509Notes

Reaction equation

[Cl:1][C:2]1[CH:11]=[C:10]([C:12](=O)[CH3:13])[C:9]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.C([O-])(=O)C.[NH4+].C([BH3-])#[N:28].[Na+]>CO.C(#N)C>[Cl:1][C:2]1[CH:11]=[C:10]([CH:12]([NH2:28])[CH3:13])[C:9]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of 1-[5-chloro-8-(3-fluorophenyl)quinolin-7-yl]ethanone (76 mg, 0.25 mmol) and ammonium acetate (195 mg, 2.54 mmol) in methanol (1.4 mL) and acetonitrile (1.4 mL) was heated at 65° C. in a sealed tube for 30 minutes. After cooling, sodium cyanoborohydride (31.9 mg, 0.507 mmol) was added to the resultant mixture. The reaction was heated at 65° C. for another 4 hours, then cooled to room temperature, quenched with saturated sodium bicarbonate, and extracted with dichloromethane. The combined extracts were dried over magnesium sulfate and then evaporated to dryness. The residue was used directly in next step (52 mg, 68%). LCMS calculated for C17H15ClFN2(M+H)+: m/z=301.1; found: 301.0.

Workup

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

Sources & evidence

ORD record: ord-f21f6449ee384bdfb18f666e307d7bae
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680108B2

Reaction notes

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