HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Water → 6,7-Dimethoxy-4-[(1-acetyl-5-indolyl)oxy]quinoline

HRID 228531
Notes
Print preview

Reaction equation

HRID 228531 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[O:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][CH:20]=[CH:19]2.[H-].[Na+].[C:27](Cl)(=[O:29])[CH3:28].O>CN(C)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][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[N:21]([C:27](=[O:29])[CH3:28])[CH:20]=[CH:19]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 24758Sodium hydrideHCID 221326454-[(1H-Indol-5-yl)oxy]-6,7-dimethoxyquinoline

Product 1

HCID 577565126,7-Dimethoxy-4-[(1-acetyl-5-indolyl)oxy]quinolineYield 41%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

6,7-Dimethoxy-4-[(1H-5-indolyl)oxy]quinoline (50 mg) was dissolved in N,N-dimethylformamide (1 ml), and 60% sodium hydride (7 mg) was added to the solution, followed by stirring under ice cooling for 30 min. Acetyl chloride (16.6 μl) was added to the reaction solution, and the mixture was stirred under ice cooling for additional one hr. Further, water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with water and saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed therefrom by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using methanol-chloroform to give the title compound (23 mg, yield 41%).

Workup

  1. stirringthe mixture was stirred under ice cooling for additional one hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was then washed with water and saturated brine
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. customThe solvent was removed
  6. distillationby distillation under the reduced pressure
  7. customthe residue was purified by thin layer chromatography

Sources & evidence

ORD record
ord-446f9ce836eb45f4a0ce4807a8401c00
Source dataset
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07560558B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes