Hydrazine hydrate (1:1) → 1-(5,7-Difluoroquinolin-6-yl)ethanamine

HRID 1892434Notes

Reaction equation

HRID 1892434 reaction equation
[F:1][C:2]1[C:11]([CH:12]([N:14]2C(=O)C3C(=CC=CC=3)C2=O)[CH3:13])=[C:10]([F:25])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.O.NN>CO>[F:1][C:2]1[C:11]([CH:12]([NH2:14])[CH3:13])=[C:10]([F:25])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 581904872-(1-(5,7-Difluoroquinolin-6-yl)ethyl)isoindoline-1,3-dione

Product 1

HCID 581905751-(5,7-Difluoroquinolin-6-yl)ethanamineYield 62.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-(1-(5,7-difluoroquinolin-6-yl)ethyl)isoindoline-1,3-dione (2.6 g, 7.7 mmol) in CH3OH (50 mL) was added hydrazine monohydrate (0.38 g, 7.7 mmol). The solution was heated at 50° C. and stirred overnight. After cooling and evaporating, the residue was purified by silica gel and eluted with hexane/EtOAc to give the title compound (1.0 g, 60%). 1H-NMR (400 MHz, DMSO-d6) δ ppm 8.95 (d, 1H), 8.45 (d, 1H), 7.65 (d, 1H), 7.60 (dd, 1H), 4.49 (q, 1H), 2.20 (bs, 2H), 1.48 (d, 3H).

Workup

  1. temperatureAfter cooling
  2. customevaporating
  3. customthe residue was purified by silica gel
  4. washeluted with hexane/EtOAc

Sources & evidence

ORD record
ord-6c76be756d274300bb7eaea65a6c71eb
Source dataset
uspto-grants-2013_08
Patent number
US08507676B2

Reaction notes

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