HCID 13206063, compound → HCID 20257386, compound

HRID 1583938Notes

Reaction equation

HRID 1583938 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]([CH3:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:5]=[CH:6][C:7]=1[NH:8][C:9]([CH3:13])([CH3:12])[C:10]#[CH:11]>O1CCOCC1.CCCCCC.[Cl-].[Zn+2].[Cl-]>[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]([CH3:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:5]=[C:6]2[C:7]=1[NH:8][C:9]([CH3:12])([CH3:13])[CH:10]=[CH:11]2

Participants

5

Reactant 1

HCID 13206063HCID 13206063, compound2×

Product 1

HCID 20257386HCID 20257386, compoundYield 93.8%

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 8058HexaneSolventHCID 312751,4-DioxaneSolvent

Procedure

6.5 g of Ethyl 2-[3-chloro-4-(1,1-dimethyl-2-propynylamino)phenyl]propionate (Compound 1) was dissolved in 70 ml of dioxane, and 10.0 g of zinc chloride were added thereto. The mixture was reacted at 95° C. for 15 hours under nitrogen atmosphere. After the reaction, the mixture was diluted with 100 ml of hexane, and subjected to column chromatography on silica gel. The solvent was distilled off to give 6.1 g of Ethyl 2-(8-chloro-1,2-dihydro-2,2-dimethylquinolin-6-yl)propionate (Compound 6).

Workup

  1. customThe mixture was reacted at 95° C. for 15 hours under nitrogen atmosphere
  2. customAfter the reaction
  3. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-4ebf843b642449faa39adb37267d28c1
Source dataset
uspto-grants-1985_11
Patent number
US04555513

Reaction notes

Loading…