Isoquinoline → Ethyl 1-(2,4,6-trimethylphenyl)-1,2-dihydro-2-isoquinolinecarboxylate

HRID 2305313Notes

Reaction equation

HRID 2305313 reaction equation
[C:1]1([CH3:11])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[Mg]Br.[CH:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][N:13]=1.Cl[C:23]([O:25][CH2:26][CH3:27])=[O:24]>C1COCC1>[CH3:11][C:1]1[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[CH:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][N:13]1[C:23]([O:25][CH2:26][CH3:27])=[O:24]

Participants

5

Reactant 3

HCID 8405IsoquinolineHCID 10928Ethyl chloroformateHCID 178425415HCID 178425415, compound

Product 1

HCID 15895522Ethyl 1-(2,4,6-trimethylphenyl)-1,2-dihydro-2-isoquinolinecarboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-mesitylmagnesium bromide in THP (1.0 M, 11 mL; 11 mmol) was added to an ice-cold solution of isoquinoline (1.3 g, 10 mmol) in THF (10 ml). After 5 minutes, ethyl chloroformate was added slowly dropwise and the mixture was further stirred at 0° for 10 min before quenched by saturated NH4CL solution. The mixture was poured into 0.5 N hydrochloric acid and extracted twice with ethyl ether. Combined organics were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo to give 3.58 g of titled compound (quantitative) as an oil which was used in the next reaction without further purification.

Workup

  1. custombefore quenched by saturated NH4CL solution
  2. additionThe mixture was poured into 0.5 N hydrochloric acid
  3. extractionextracted twice with ethyl ether
  4. washCombined organics were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-67edd1157e05431b816c464a60320fa2
Source dataset
uspto-grants-2002_08
Patent number
US06440969B2

Reaction notes

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