Hydrazine hydrate (1:1) → 6-(Aminomethyl)quinoline

HRID 1892284

Reaction equation

HRID 1892284 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([CH2:11][N:12]3C(=O)C4C(=CC=CC=4)C3=O)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.O.NN>CO>[N:1]1[C:10]2[C:5](=[CH:6][C:7]([CH2:11][NH2:12])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 230792942-(Quinolin-6-ylmethyl)isoindoline-1,3-dione

Product 1

HCID 15143846-(Aminomethyl)quinolineYield 45.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-(quinolin-6-ylmethyl)isoindoline-1,3-dione (20 g, 69.4 mmol) in MeOH (100 mL) was added hydrazine monohydrate (3.47 g, 69.4 mmol). The solution was heated at reflux for 3 h, then cooled to it and filtered through celite. The filtrate was concentrated in vacuo. EtOAc then was added to the residue and the resulting solution was filtered and concentrated in vacuo to afford 5 g (41%) of the title compound. LCMS (method B): [MH]+=159, tR=0.93 min.

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 3 h
  3. temperaturecooled to it
  4. filtrationfiltered through celite
  5. concentrationThe filtrate was concentrated in vacuo
  6. additionEtOAc then was added to the residue
  7. filtrationthe resulting solution was filtered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-825378f923b442beb0f776301f894aa8
Source dataset
uspto-grants-2013_08
Patent number
US08507676B2

Linked notes

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