Hydrazine hydrate (1:1) → 1-(3-aminopropyl)-5-fluoro-3-(4-methoxyphenyl)-8-propoxy-1H-quinolin-4-one

HRID 68152Notes

Reaction equation

HRID 68152 reaction equation
O.NN.[F:4][C:5]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][CH3:18])=[C:11]2[C:6]=1[C:7](=[O:41])[C:8]([C:33]1[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=1)=[CH:9][N:10]2[CH2:19][CH2:20][CH2:21][N:22]1C(=O)C2C(=CC=CC=2)C1=O>C(O)C>[NH2:22][CH2:21][CH2:20][CH2:19][N:10]1[C:11]2[C:6](=[C:5]([F:4])[CH:14]=[CH:13][C:12]=2[O:15][CH2:16][CH2:17][CH3:18])[C:7](=[O:41])[C:8]([C:33]2[CH:34]=[CH:35][C:36]([O:39][CH3:40])=[CH:37][CH:38]=2)=[CH:9]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 584924242-{3-[5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-4H-quinolin-1-yl]propyl}isoindole-1,3-dione

Product 1

HCID 584925271-(3-aminopropyl)-5-fluoro-3-(4-methoxyphenyl)-8-propoxy-1H-quinolin-4-oneYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydrazine hydrate (0.62 ml, 12.8 mmol) was added to an ethanol solution (60 ml) of 2-{3-[5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-4H-quinolin-1-yl]propyl}isoindole-1,3-dione (2.0 g, 3.88 mmol) and heated under reflux for 4 hours. The resulting mixture was concentrated under reduced pressure, a 5N aqueous sodium hydroxide solution was added to the thus-obtained residue, and then the resulting mixture was subjected to extraction using dichloromethane. The thus-obtained organic layer was sequentially washed with water and an aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure, giving a yellow oily 1-(3-aminopropyl)-5-fluoro-3-(4-methoxyphenyl)-8-propoxy-1H-quinolin-4-one (1.4 g, yield: 94%).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 4 hours
  3. concentrationThe resulting mixture was concentrated under reduced pressure
  4. additiona 5N aqueous sodium hydroxide solution was added to the thus-obtained residue
  5. extractionthe resulting mixture was subjected to extraction
  6. washThe thus-obtained organic layer was sequentially washed with water
  7. dry with materialan aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-51517834f70f4e848ca03048712def70
Source dataset
uspto-grants-2014_09
Patent number
USRE045108E1

Reaction notes

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