Hydrazine → 7-Bromoquinolin-3-amine

HRID 1525925Notes

Reaction equation

HRID 1525925 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([N:12]3C(=O)C4C(=CC=CC=4)C3=O)[CH:8]=[N:9]2)=[CH:4][CH:3]=1.NN>C(O)C>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([NH2:12])[CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 690851162-(7-Bromoquinolin-3-yl)isoindoline-1,3-dione

Product 1

HCID 525543797-Bromoquinolin-3-amineYield 56%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 2-(7-bromoquinolin-3-yl)isoindoline-1,3-dione (10 g, 28.3 mmol) in ethanol (200 mL) was treated with hydrazine (1.777 mL, 56.6 mmol) then heated under reflux for 1 h. The mixture was allowed to cool, the precipitate was collected and washed with a little ethanol, and the filtrate was evaporated to a grey solid. The isolated solid was dissolved in warm ethanol and adsorbed onto silica gel. Purification of the solid by silica gel chromatography (50-100% ethyl acetate/hexanes) afforded the title compound (3.5 g, 56%). 1H NMR (400 MHz, DMSO-d6) δ ppm 5.83 (s, 2 H) 7.14 (d, J=2.53 Hz, 1 H) 7.49 (dd, J=8.84, 2.02 Hz, 1 H) 7.54-7.65 (m, 1 H) 7.94 (d, J=1.77 Hz, 1 H) 8.46 (d, J=2.78 Hz, 1 H).

Workup

  1. temperaturethen heated
  2. temperatureunder reflux for 1 h
  3. temperatureto cool
  4. customthe precipitate was collected
  5. washwashed with a little ethanol
  6. customthe filtrate was evaporated to a grey solid
  7. dissolutionThe isolated solid was dissolved in warm ethanol
  8. customPurification of the solid by silica gel chromatography (50-100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-26d5ad71e3894843aef132bd24fa18a0
Source dataset
uspto-grants-2015_07
Patent number
US09084794B2

Reaction notes

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