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

HRID 1959758Notes

Reaction equation

HRID 1959758 reaction equation
[F:1][C:2]1[C:11]([CH2:12][N:13]2C(=O)C3C(=CC=CC=3)C2=O)=[C:10]([F:24])[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]([CH2:12][NH2:13])=[C:10]([F:24])[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 698103402-(5,7-Difluoroquinolin-6-ylmethyl)isoindoline-1,3-dione

Product 1

HCID 66994774(5,7-Difluoroquinolin-6-yl)methanamineYield 88.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-(5,7-difluoroquinolin-6-ylmethyl)isoindoline-1,3-dione (5.10 g, 15.73 mmol) in CH3OH (150 mL) was added hydrazine monohydrate (0.50 g, 15.73 mmol). The solution was heated at reflux for 3 h. After cooling, the mixture was filtered through celite. The filtrate was concentrated in vacuo. EtOAc was added to dilute the residue, filtered and concentrated in vacuo to afford (5,7-difluoroquinolin-6-yl)methanamine (2.70 g, 88%). 1H-NMR (400 MHz, CDCl3) δ ppm 8.93 (d, 1H), 8.38 (d, 1H), 7.59 (d, 1H), 7.43 (m, 1H), 4.12 (s, 2H). LCMS (method B): [MH]+=195.0, tR=0.17 min.

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 3 h
  3. temperatureAfter cooling
  4. filtrationthe mixture was filtered through celite
  5. concentrationThe filtrate was concentrated in vacuo
  6. additionEtOAc was added
  7. additionto dilute the residue
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-99ddfd0ec0f44ce89739c4d09fae7067
Source dataset
uspto-grants-2013_04
Patent number
US08410264B2

Reaction notes

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