Iodine chloride → HCID 49806332, compound

HRID 2381210Notes

Reaction equation

HRID 2381210 reaction equation
[CH3:1][O:2][C:3]1[C:23]2[C:22]([CH3:25])([CH3:24])[N:10]3[CH2:11][CH2:12][C:13]4[C:18]([C:9]3=[CH:8][C:7]=2[CH:6]=[CH:5][C:4]=1[O:26][CH3:27])=[CH:17][C:16]1[O:19][CH2:20][O:21][C:15]=1[CH:14]=4.I[Cl:29]>ClCCl>[Cl:29][C:6]1[C:7]2[CH:8]=[C:9]3[C:18]4[C:13](=[CH:14][C:15]5[O:21][CH2:20][O:19][C:16]=5[CH:17]=4)[CH2:12][CH2:11][N:10]3[C:22]([CH3:24])([CH3:25])[C:23]=2[C:3]([O:2][CH3:1])=[C:4]([O:26][CH3:27])[CH:5]=1

Participants

4

Reactant 2

HCID 24640Iodine chlorideHCID 49806452HCID 49806452, compound

Product 1

HCID 49806332HCID 49806332, compoundYield 4.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 9,10-dimethoxy-8,8-dimethyl-5,8-dihydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline (182 mg, 0.5 mmol) in anhydrous dichloromethane (20 mL) at 25° C. was added Iodine monochloride (0.57 g, 3.5 mmol). After stirring in the dark at 25° C. for 72 h, the reaction was washed twice with aqueous 10% sodium thiosulfate solution (2×50 mL) to remove excessive iodine monochloride, dried over anhydrous sodium sulfate and concentrated in vacuo. Purification by Waters Automated Flash System (column: Xterra 30 mm×100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% ammonium hydroxide in water) afforded 12-chloro-9,10-dimethoxy-8,8-dimethyl-5,8-dihydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline (9.6 mg, 4%). LC/MS m/e calcd for C22H22ClNO4 (M+H)+: 400.88, observed: 400.1; 1H NMR (400 MHz, MeOD) δ ppm 2.05 (s, 6 H) 3.14 (m, 2 H) 3.93 (s, 3 H) 4.01 (s, 3 H) 4.23 (m, 2 H) 6.22 (s, 2 H) 7.04 (s, 1 H) 7.32 (s., 1 H) 7.63 (s, 1 H).

Workup

  1. washthe reaction was washed twice with aqueous 10% sodium thiosulfate solution (2×50 mL)
  2. customto remove excessive iodine monochloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customPurification by Waters Automated Flash System (column: Xterra 30 mm×100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% ammonium hydroxide in water)

Sources & evidence

ORD record
ord-1d9185ae1bf949c19eaa8ee28f5c8e7e
Source dataset
uspto-grants-2012_09
Patent number
US08258149B2

Reaction notes

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