Dimethylformamide → HCID 20484908, compound

HRID 647439Notes

Reaction equation

HRID 647439 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([Cl:12])[CH:10]=2)[CH:5]=[C:4]([NH:13][C:14]2[CH:27]=[CH:26][C:17]([O:18][CH:19]([CH3:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:16][CH:15]=2)[N:3]=1.[H-].[Na+].CN(C)C=O.[CH2:35](I)[CH3:36]>C(OCC)(=O)C>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([Cl:12])[CH:10]=2)[CH:5]=[C:4]([N:13]([C:14]2[CH:15]=[CH:16][C:17]([O:18][CH:19]([CH3:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:26][CH:27]=2)[CH2:35][CH3:36])[N:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 13386228HCID 13386228, compound

Product 1

HCID 20484908HCID 20484908, compoundYield 103.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of ethyl 2-{4-[N-(1,7-dichloroisoquinolin-3-yl)amino]phenoxy}propionate (0.36 g), sodium hydride (0.05 g, 60%) and dimethylformamide (10 ml) was stirred at room temperature for 15 minutes. Ethyl iodide (0.17 g) was added and stirring was continued for a further 15 minutes. The mixture was then poured into ethyl acetate and washed with water, dried (MgSO4) and evaporated. Purification by column chromatography over silica gel gave ethyl 2-{4-[N-(1,7-dichloroisoquinolin-3-yl)-N-ethylamino]phenoxy}propionate as a yellow oil (0.40 g).

Workup

  1. stirringstirring
  2. waitwas continued for a further 15 minutes
  3. washwashed with water
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customPurification by column chromatography over silica gel

Sources & evidence

ORD record
ord-b417f19dfafd4fa0a1037f08dbd57dfb
Source dataset
uspto-grants-1983_10
Patent number
US04409017

Reaction notes

Loading…