Sodium Carbonate → 6-Bromo-N-(6-methoxy-4-methyl-8-quinolinyl)hexanamide

HRID 1706906Notes

Reaction equation

HRID 1706906 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([O:13][CH3:14])[CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[C:7]2[CH3:12].C(=O)([O-])[O-].[Na+].[Na+].[Br:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27](Cl)=[O:28]>CC(C)=O>[Br:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([NH:1][C:2]1[CH:3]=[C:4]([O:13][CH3:14])[CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[C:7]2[CH3:12])=[O:28]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 898486-Bromohexanoyl chlorideHCID 6047536-Methoxy-4-methyl-8-quinolinamine

Product 1

HCID 6120236-Bromo-N-(6-methoxy-4-methyl-8-quinolinyl)hexanamideYield 61%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a mixture of 9.4 g (0.05 mol) of 8-amino-6-methoxy-4-methylquinoline and 8.7 g (0.082 mol) of anhydrous sodium carbonate in 60 ml of acetone was added dropwise a solution of 6-bromohexanoylchloride in 35 ml of acetone. The mixture was heated under reflux for 4 hours, cooled and filtered. The filter cake was washed with with chloroform and the filtrate and wash were combined and concentrated in vacuo to dryness. The residual solid was recrystallized first from ethanol and then from 85% aqueous ethanol to give 10.8 g (61%) of product, mp 111°-113°.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 4 hours
  3. temperaturecooled
  4. filtrationfiltered
  5. washThe filter cake was washed with with chloroform
  6. washthe filtrate and wash
  7. concentrationconcentrated in vacuo to dryness
  8. customThe residual solid was recrystallized first from ethanol

Sources & evidence

ORD record
ord-750aba5e37414f35acb83b7b2241d11d
Source dataset
uspto-grants-1980_06
Patent number
US04209519

Reaction notes

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