Iodine → HCID 15917418, compound

HRID 648089Notes

Reaction equation

HRID 648089 reaction equation
[Mg].II.[F:4][C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[CH2:7][Cl:8].[CH3:13][N:14]1[CH2:23][C:22](=[O:24])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15]1>CCOCC>[ClH:8].[F:4][C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[CH2:7][C:22]1([OH:24])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][N:14]([CH3:13])[CH2:23]1

Participants

6

Reactant 4

HCID 807IodineHCID 9580Benzene, 1-(chloromethyl)-2-fluoro-2×HCID 5462224MagnesiumHCID 106308122-Methyl-2,3-dihydroisoquinolin-4(1H)-one

Product 1

HCID 15917418HCID 15917418, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

To a suspension of magnesium shavings (3.96 g) and a crystal of iodine in anhydrous ether (50 ml) is added several milliliters of 2-fluorobenzyl chloride. After initiation of the reaction with a hot air gun, the remainder of the 2-fluorobenzyl chloride for a total of 27.2 g is added dropwise as a solution in ether (50 ml). After the addition is complete, the reaction mixture is refluxed for 2 hours. A solution of 2-methyl-2,3-dihydro-4(1H)-isoquinolone (24.2 g) in ether (100 ml) is added dropwise at room temperature. The granular precipitate which forms is stirred at room temperature for one hour, filtered and washed with ether. The solid is hydrolyzed by stirring at room temperature for one hour with an ammonium chloride solution, followed by ether extraction. The ether extract is washed with saturated sodium chloride solution and dried over anhydrous magnesium sulfate. Removal of the ether yields 28.6 g of an oil. A portion of the oil (5 g) is dissolved in ether, filtered, and ethereal hydrogen chloride is added to give product as a white powder (5.5 g, 97%), mp 105°.

Workup

  1. customAfter initiation of the reaction with a hot air gun
  2. additionAfter the addition
  3. temperaturethe reaction mixture is refluxed for 2 hours
  4. filtrationfiltered
  5. washwashed with ether
  6. stirringby stirring at room temperature for one hour with an ammonium chloride solution
  7. extractionfollowed by ether extraction
  8. extractionThe ether extract
  9. washis washed with saturated sodium chloride solution
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customRemoval of the ether

Sources & evidence

ORD record
ord-0cc5c266da3b41e1a7e3d4b837f0180e
Source dataset
uspto-grants-1983_10
Patent number
US04410699

Reaction notes

Loading…