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

HRID 75367
Notes
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Reaction equation

HRID 75367 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 9321HydrazineHCID 866985072-((S)-1-(7-fluoro-2-(pyridin-2-yl)quinolin-3-yl)ethyl)isoindoline-1,3-dione

Product 1

HCID 86698506(S)-1-(7-Fluoro-2-(pyridin-2-yl)quinolin-3-yl)ethan-1-amineYield 71%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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

  1. temperaturecooled to rt
  2. filtrationThe reaction mixture was filtered
  3. washwashed with EtOAc
  4. washThe resulting EtOAc solution was washed with water, brine
  5. dry with materialdried over Na2SO4
  6. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes