Chloride → HCID 49806452, compound

HRID 2381219Notes

Reaction equation

HRID 2381219 reaction equation
Cl[CH:2]1[NH+:11]2[CH2:12][CH2:13][C:14]3[C:19]([C:10]2=[CH:9][C:8]2[CH:7]=[CH:6][C:5]([O:23][CH3:24])=C(OC)[C:3]1=2)=[CH:18][C:17]1[O:20][CH2:21][O:22][C:16]=1[CH:15]=3.[Cl-].C[Mg]Cl.O1CCC[CH2:32]1.[CH2:36]([O:38][CH2:39][CH3:40])C>>[CH3:36][O:38][C:39]1[C:40]2[C:2]([CH3:3])([CH3:32])[N:11]3[CH2:12][CH2:13][C:14]4[C:19]([C:10]3=[CH:9][C:8]=2[CH:7]=[CH:6][C:5]=1[O:23][CH3:24])=[CH:18][C:17]1[O:20][CH2:21][O:22][C:16]=1[CH:15]=4

Participants

6

Reactant 5

HCID 312ChlorideHCID 3283Diethyl EtherHCID 8028TetrahydrofuranHCID 86647495HCID 86647495, compoundHCID 178418332HCID 178418332, compound

Product 1

HCID 49806452HCID 49806452, compoundYield 87%

Conditions

Temperature
0 °C

Procedure

To a suspension of 8-chloro-9,10-dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ylium; chloride (2 g, 5 mmol) in anhydrous diethyl ether (150 mL) at 0° C. was added a solution of methylmagnesium chloride in tetrahydrofuran (3 M, 18 mL, 54 mmol) dropwise. After stirring at 0° C. for 30 min, the reaction was quenched by adding saturated aqueous ammonium chloride solution (50 mL). The mixture was extracted with diethyl ether (2×100 mL), washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was re-crystallized from diethyl ether to afford 9,10-dimethoxy-8,8-dimethyl-5,8-dihydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline (1.6 g, 87%). LC/MS m/e calcd for C22H23NO4 (M+H)+: 366.43, observed: 366.0; 1H NMR (400 MHz, DMSO-d6) δ ppm 1.65 (s, 6 H) 2.73 (t, J=5.56 Hz, 2 H) 3.27 (t, J=5.56 Hz, 2 H) 3.76 (s, 6 H) 5.69 (s, 1 H) 5.99 (s, 2 H) 6.59 (d, J=8.34 Hz, 1 H) 6.74 (s, 1 H) 6.81 (d, J=8.34 Hz, 1 H) 7.21 (s, 1 H).

Workup

  1. customthe reaction was quenched
  2. additionby adding saturated aqueous ammonium chloride solution (50 mL)
  3. extractionThe mixture was extracted with diethyl ether (2×100 mL)
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was re-crystallized from diethyl ether

Sources & evidence

ORD record
ord-4e200ef8f7a24dc598d44d41c2fc0e14
Source dataset
uspto-grants-2012_09
Patent number
US08258149B2

Reaction notes

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