Iodine → HCID 15917420, compound

HRID 648094Notes

Reaction equation

HRID 648094 reaction equation
[Mg].II.[Cl:4][C:5]1[CH:12]=[CH:11][C:8]([CH2:9]Br)=[C:7]([F:13])[CH:6]=1.[CH3:14][N:15]1[CH2:24][C:23](=[O:25])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16]1>CCOCC>[Cl:4][C:5]1[CH:12]=[CH:11][C:8]([CH2:9][C:23]2([OH:25])[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:16][N:15]([CH3:14])[CH2:24]2)=[C:7]([F:13])[CH:6]=1

Participants

6

Reactant 4

HCID 807IodineHCID 27365514-Chloro-2-fluorobenzyl bromideHCID 5462224MagnesiumHCID 106308122-Methyl-2,3-dihydroisoquinolin-4(1H)-one

Product 1

HCID 15917420HCID 15917420, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent4×

Procedure

To a suspension of magnesium shavings (15.7 g) and a few crystals of iodine in anhydrous ether (200 ml) is slowly dropped 4-chloro-2-fluorobenzylbromide (146.0 g) in anhydrous ether (200 ml) at such a rate so as to maintain the ether reflux. After the addition is complete, the reaction mixture is heated under reflux for two hours. A solution of 2-methyl-2,3-dihydro-4(1H)-isoquinolone (70.2 g) in anhydrous ether (200 ml) is slowly added dropwise. After the addition is complete, the reaction mixture is heated under reflux for three hours. The reaction mixture, after cooling, is stirred in 1.5 l. saturated ammonium chloride and extracted with ether. The combined ether extracts are washed with water (2x), saturated sodium chloride solution and dried over anhydrous magnesium sulfate. After filtering, the solvent is removed to yield a solid, which upon trituration with petroleum ether, yields the product (109.5 g, 82%), mp 113°-116°. An analytical sample is recrystallized from anhydrous ether to yield needles, mp 116°-117°.

Workup

  1. temperaturereflux
  2. additionAfter the addition
  3. temperaturethe reaction mixture is heated
  4. temperatureunder reflux for two hours
  5. additionAfter the addition
  6. temperaturethe reaction mixture is heated
  7. temperatureunder reflux for three hours
  8. temperatureThe reaction mixture, after cooling
  9. extractionsaturated ammonium chloride and extracted with ether
  10. washThe combined ether extracts are washed with water (2x), saturated sodium chloride solution
  11. dry with materialdried over anhydrous magnesium sulfate
  12. filtrationAfter filtering
  13. customthe solvent is removed
  14. customto yield a solid, which upon trituration with petroleum ether

Sources & evidence

ORD record
ord-9e2096ee58c14534b4e8e11588518f62
Source dataset
uspto-grants-1983_10
Patent number
US04410699

Reaction notes

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