Dimethylamine → HCID 15766890, compound

HRID 1292015Notes

Reaction equation

HRID 1292015 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][CH2:13]/[CH:14]=[CH:15]/[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[CH3:21][NH:22][CH3:23].[OH-].[Na+]>O.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH:14]([N:22]([CH3:23])[CH3:21])[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

7

Reactant 3

HCID 674DimethylamineHCID 14798Sodium HydroxideHCID 67739237HCID 67739237, compound

Product 1

HCID 15766890HCID 15766890, compoundYield 15%

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A mixture of 5.8 g (20 mmol) of ethyl (E)-4-(5-chloroquinoline-8-yloxy)-2-butenoate, 20 ml of a 60% solution of dimethylamine in water and 0.34 g (1.0 mmol) of tetrabutylammonium hydrogen sulfate in 50 ml of dichloromethane, 40 ml of water and 10 ml of 2N sodium hydroxide solution was allowed to stand for two days at room temperature. The organic phase was separated off, and the aqueous phase was extracted twice using dichloromethane. After drying over magnesium sulfate, the solvent was stripped off in vacuo and the residue obtained was chromatographed on silica gel (ethyl acetate:heptane 7:3; followed by ethyl acetate). 1.0 g (15%) of the title compound was obtained as an oil.

Workup

  1. customThe organic phase was separated off
  2. extractionthe aqueous phase was extracted twice using dichloromethane
  3. dry with materialAfter drying over magnesium sulfate
  4. customthe residue obtained
  5. customwas chromatographed on silica gel (ethyl acetate:heptane 7:3; followed by ethyl acetate)

Sources & evidence

ORD record
ord-77ca2b8ca92246b6acb067ff5b3b74de
Source dataset
uspto-grants-1998_05
Patent number
US05756422

Reaction notes

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