Tetrahydrofuran → HCID 22503419, compound

HRID 1006957Notes

Reaction equation

HRID 1006957 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11](Cl)[C:12]3[C:17]([CH:18]=2)=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:5][CH:4]=1.[Cl-].[NH4+].O1CCC[CH2:23]1>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([CH3:23])[C:12]3[C:17]([CH:18]=2)=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 225026591-Chloro-3-(4-methoxyphenyl)isoquinoline

Product 1

HCID 22503419HCID 22503419, compoundYield 100%

Procedure

3-(4-Methoxyphenyl)-1-chloroisoquinoline (3.25 g) was dissolved in tetrahydrofuran (30 ml), followed by the addition of 3.0M ethylmagnesium bromide diethyl ether solution (12 ml) and NiCl2-(dppp) (50 mg) at 0° C. After the mixture was reacted overnight at room temperature, the resulting reaction solution was poured into an aqueous solution of saturated ammonium chloride and extracted with ethyl acetate. The resulting organic layer was washed with water and brine, dried and evaporated, to give 3-(4-methoxyphenyl)-1-methylisoquinoline as an oil (3.3 g, yield; 100%).

Workup

  1. customAfter the mixture was reacted overnight at room temperature
  2. customthe resulting reaction solution
  3. extractionextracted with ethyl acetate
  4. washThe resulting organic layer was washed with water and brine
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-7211ff2f64e1448c88b214bb8227654d
Source dataset
uspto-grants-2004_09
Patent number
US06790844B2

Reaction notes

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