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

HRID 276101Notes

Reaction equation

HRID 276101 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 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 2-mesitylmagnesium bromide in THF (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° C. 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-c095728ba5b94c78a7f6bb6e6e0451a7
Source dataset
uspto-grants-2002_03
Patent number
US06353103B1

Reaction notes

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