Hydrazine → (S)-1-(7-Fluoro-2-(pyridin-2-yl)quinolin-3-yl)ethan-1-amine

HRID 75367Notes

Reaction equation

[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C@@H:18]([N:20]3C(=O)C4C(=CC=CC=4)C3=O)[CH3:19])[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=3)=[N:9]2)=[CH:4][CH:3]=1.NN>C(O)C>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C@@H:18]([NH2:20])[CH3:19])[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=3)=[N:9]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a slurried 2-((S)-1-(7-fluoro-2-(pyridin-2-yl)quinolin-3-yl)ethyl)isoindoline-1,3-dione (2.1 g, 5.3 mmol) in anhydrous ethanol (15 mL) was added NH2NH2 (0.85 g, 26 mmol) dropwise over 5 minutes. The reaction mixture was heated to 90° C. for 30 min and cooled to rt. The reaction mixture was filtered and washed with EtOAc. The resulting EtOAc solution was washed with water, brine and dried over Na2SO4. Removal of solvents gave a tan oil of (S)-1-(7-fluoro-2-(pyridin-2-yl)quinolin-3-yl)ethanamine (1 g, 71%). Mass Spectrum (ESI) m/e=468 (M+1).

Workup

temperaturecooled to rt
filtrationThe reaction mixture was filtered
washwashed with EtOAc
washThe resulting EtOAc solution was washed with water, brine
dry with materialdried over Na2SO4
customRemoval of solvents

Sources & evidence

ORD record: ord-96cc485101af4d57993b454e27f35b73
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835432B2

Reaction notes

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