Triethylamine → Isoquinoline, 7-(chloromethyl)-

HRID 2417551Notes

Reaction equation

HRID 2417551 reaction equation
C(O[C:4]([C:6]1[CH:15]=[C:14]2[C:9]([CH:10]=[CH:11][N:12]=[CH:13]2)=[CH:8][CH:7]=1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(N(CC)CC)C.CS([Cl:33])(=O)=O>C(O)C.ClCCl.O>[Cl:33][CH2:4][C:6]1[CH:15]=[C:14]2[C:9]([CH:10]=[CH:11][N:12]=[CH:13]2)=[CH:8][CH:7]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 21226445Aluminium lithium hydrideHCID 22632542Ethyl isoquinoline-7-carboxylate

Product 1

HCID 22632426Isoquinoline, 7-(chloromethyl)-

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

196 mg (0.97 mmol) of 7-ethoxycarbonylisoquinoline obtained in step 1 was dissolved in 15 ml of ethanol. 110 mg (2.9 mmol) of lithium aluminum hydride was added to the solution under cooling with ice, and they were stirred at room temperature for 2 hours. Water was added to the reaction mixture and they were stirred for 2 hours. The reaction solution was filtered, and the filtrate was concentrated. The obtained oily product was dissolved in 10 ml of dichloromethane. 0.26 ml (1.9 mmol) of triethylamine and 0.1 ml (1.3 mmol) of methanesulfonyl chloride were added to the obtained solution, and they were stirred overnight. After the treatment with dichloromethane as the extracting solvent by an ordinary method, the crude product was obtained.

Workup

  1. temperatureunder cooling with ice, and they
  2. stirringwere stirred for 2 hours
  3. filtrationThe reaction solution was filtered
  4. concentrationthe filtrate was concentrated
  5. dissolutionThe obtained oily product was dissolved in 10 ml of dichloromethane
  6. stirringwere stirred overnight

Sources & evidence

ORD record
ord-134fd3e6364043be9145b1d300494c31
Source dataset
uspto-grants-2004_11
Patent number
US06825191B2

Reaction notes

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