Dimethylformamide → 2-{3-[5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-4H-quinolin-1-yl]propyl}isoindole-1,3-dione

HRID 68151Notes

Reaction equation

HRID 68151 reaction equation
[H-].[Na+].CN(C=O)C.[F:8][C:9]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH3:22])=[C:15]2[C:10]=1[C:11](=[O:31])[C:12]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1)=[CH:13][NH:14]2.Br[CH2:33][CH2:34][CH2:35][N:36]1[C:40](=[O:41])[C:39]2=[CH:42][CH:43]=[CH:44][CH:45]=[C:38]2[C:37]1=[O:46]>C(OCC)(=O)C.O>[F:8][C:9]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH3:22])=[C:15]2[C:10]=1[C:11](=[O:31])[C:12]([C:23]1[CH:24]=[CH:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=1)=[CH:13][N:14]2[CH2:33][CH2:34][CH2:35][N:36]1[C:40](=[O:41])[C:39]2[C:38](=[CH:45][CH:44]=[CH:43][CH:42]=2)[C:37]1=[O:46]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 21611N-3-BromopropylphthalimideHCID 24758Sodium hydrideHCID 251656785-fluoro-3-(4-methoxyphenyl)-8-propoxy-1H-quinolin-4-one

Product 1

HCID 584924242-{3-[5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-4H-quinolin-1-yl]propyl}isoindole-1,3-dioneYield 59.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (60% oil base, 800 mg, 18.3 mmol) was added to a DMF solution (25 ml) of 5-fluoro-3-(4-methoxyphenyl)-8-propoxy-1H-quinolin-4-one (5.0 g, 15.2 mmol). The mixture was stirred for 30 minutes at room temperature. N-Bromopropyl phthalimide (4.48 g, 16.7 mmol) was added to the mixture and stirred at room temperature for 30 minutes and at 50° C. for 5 hours. The reaction mixture was ice-cooled and water (20 ml) and ethyl acetate were added thereto, followed by stirring for 2 hours. The generated insoluble matter was separated, washed with water, and then dried, giving a pale yellow powder of 2-{3-[5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-4H-quinolin-1yl]propyl}isoindole-1,3-dione (4.63 g, yield: 59%).

Workup

  1. stirringstirred at room temperature for 30 minutes and at 50° C. for 5 hours
  2. temperaturecooled
  3. stirringby stirring for 2 hours
  4. customThe generated insoluble matter was separated
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-18e870cf342740df9064a15e441aa92a
Source dataset
uspto-grants-2014_09
Patent number
USRE045108E1

Reaction notes

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