Hydrazine hydrate (1:1) → 1-(5-Chloro-2-(pyridin-2-yl)quinolin-3-yl)ethanamine

HRID 216804Notes

Reaction equation

HRID 216804 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([CH:18]([N:20]1C(=O)C3C(=CC=CC=3)C1=O)[CH3:19])[C:6]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1)=[N:7]2.O.NN>CCO>[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([CH:18]([NH2:20])[CH3:19])[C:6]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1)=[N:7]2

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 577078282-(1-(5-Chloro-2-(pyridin-2-yl)quinolin-3-yl)ethyl)isoindoline-1,3-dione

Product 1

HCID 577079431-(5-Chloro-2-(pyridin-2-yl)quinolin-3-yl)ethanamineYield 68.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

2-(1-(5-Chloro-2-(pyridin-2-yl)quinolin-3-yl)ethyl)isoindoline-1,3-dione (220 mg, 532 μmol) was added to EtOH. To the resulting slurry was added hydrazine hydrate (133 μl, 2658 μmol) and the mixture was heated in an oil bath at 80° C. for 3 h. The reaction mixture was cooled to room temperature, filtered, and rinsed with EtOH (10 mL). The filtrate was acidified with 1.0 N HCl (˜5 mL) and concentrated on the rotavap to remove ethanol. A minor amount of solid precipitated and was removed by filtration. The filtrate was neutralized with solid sodium carbonate and extracted (2×) with DCM:IPA (4:1). The organic extracts were dried with sodium sulfate, filtered and concentrated to obtain 103 mg (68%) of a solid/film. LC-MS (+esi, M+H+=284.0). 1H NMR (400 MHz, DICHLOROMETHANE-d2) δ ppm 1.42 (d, J=6.65 Hz, 3H) 4.71 (q, J=6.65 Hz, 1H) 7.38-7.42 (m, 1H) 7.60-7.68 (m, 2H) 7.88-7.97 (m, 2H) 8.02 (dq, J=7.78, 0.80 Hz, 1H) 8.68-8.71 (m, 1H) 8.82 (t, J=0.78 Hz, 1H). LC-MS (+esi, M+H+=284.0).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered
  3. washrinsed with EtOH (10 mL)
  4. concentrationconcentrated on the rotavap
  5. customto remove ethanol
  6. customA minor amount of solid precipitated
  7. customwas removed by filtration
  8. extractionextracted (2×) with DCM:IPA (4:1)
  9. dry with materialThe organic extracts were dried with sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-ede3de5c4da94b67b006bf4a1a0bf348
Source dataset
uspto-grants-2012_06
Patent number
US08193199B2

Reaction notes

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