HCID 22646593, compound → 6-Methoxy-7-(3-morpholinopropoxy)quinolin-4-ol

HRID 393610Notes

Reaction equation

HRID 393610 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:12]=[C:13]([CH:26]=[CH:27][C:28]=2[O:29][CH3:30])[NH:14][CH:15]=[C:16]2[C:21](=[O:22])OC(C)(C)OC2=O)[CH2:3][CH2:2]1>C1(OC2C=CC=CC=2)C=CC=CC=1>[CH3:30][O:29][C:28]1[CH:27]=[C:26]2[C:13](=[CH:12][C:11]=1[O:10][CH2:9][CH2:8][CH2:7][N:4]1[CH2:3][CH2:2][O:1][CH2:6][CH2:5]1)[NH:14][CH:15]=[CH:16][C:21]2=[O:22]

Participants

3

Reactant 1

HCID 22646593HCID 22646593, compound

Product 1

HCID 226466086-Methoxy-7-(3-morpholinopropoxy)quinolin-4-olYield 41%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Procedure

A solution of 5-((3-(3-morpholinopropoxy)-4-methoxyanilino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione (700 mg, 1.66 mmol) in phenyl ether (5 ml) was heated at reflux for 2 minutes. After cooling, the residue was triturated with ether and acetone. The solid was collected by filtration, washed with acetone followed by ether and dried under vacuum to give 6-methoxy-7-(3-morpholinopropoxy)-1,4-dihydroquinolin-4-one (207 mg, 41%).

Workup

  1. temperatureat reflux for 2 minutes
  2. temperatureAfter cooling
  3. customthe residue was triturated with ether and acetone
  4. filtrationThe solid was collected by filtration
  5. washwashed with acetone
  6. customdried under vacuum

Sources & evidence

ORD record
ord-76a88ce9e11c4cc09519d323c5c501ea
Source dataset
uspto-grants-2004_10
Patent number
US06809097B1

Reaction notes

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