Potassium Carbonate → N-(3-(6,7-dimethoxyquinolin-4-yloxy)propyl)phthalimide

HRID 387740

Reaction equation

HRID 387740 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[OH:15].Br[CH2:17][CH2:18][CH2:19][N:20]1[C:24](=[O:25])[C:23]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:22]2[C:21]1=[O:30].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C.CN(C)C=O>O1CCCC1.C(OCC)(=O)C.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][CH2:17][CH2:18][CH2:19][N:20]1[C:24](=[O:25])[C:23]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:22]2[C:21]1=[O:30]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 21611N-3-BromopropylphthalimideHCID 17824068DMF dimethylformamideHCID 178486804HCID 178486804, compound

Product 1

HCID 22936492N-(3-(6,7-dimethoxyquinolin-4-yloxy)propyl)phthalimideYield 14.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

6,7-Dimethoxy-4-hydroxyquinoline (4.0 g, 19.5 mM), N-(3-bromopropyl)phthalimide (5.8 g, 21.5 mM), potassium carbonate (5.4 g, 39 mM) and DMF dimethylformamide (20 ml) were stirred at 60° C. for 1.5 hours. Water, ethyl acetate and tetrahydrofuran were added to the reaction solution for extraction. The solid which precipitated after standing for a period was filtered out to obtain N-(3-(6,7-dimethoxyquinolin-4-yloxy)propyl)phthalimide (1.1 g).

Workup

  1. customThe solid which precipitated
  2. waitafter standing for a period
  3. filtrationwas filtered out

Sources & evidence

ORD record
ord-3c52d6157410407d814006309460fd28
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Linked notes

Loading…