Chloride → HCID 49806218, compound

HRID 2381208Notes

Reaction equation

HRID 2381208 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:4]([O:25][CH3:26])[C:3]1=2)=[CH:18][C:17]1[O:20][CH2:21][O:22][C:16]=1[CH:15]=3.[Cl-].[CH2:28]([Mg]Cl)[CH:29]=[CH2:30].O1C[CH2:36][CH2:35][CH2:34]1>C(OCC)C>[CH2:28]([C:2]1([CH2:36][CH:35]=[CH2:34])[N: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:4]([O:25][CH3:26])[C:3]1=2)=[CH:18][C:17]1[O:20][CH2:21][O:22][C:16]=1[CH:15]=3)[CH:29]=[CH2:30]

Participants

6

Reactant 4

HCID 312ChlorideHCID 8028TetrahydrofuranHCID 86647495HCID 86647495, compoundHCID 178418473HCID 178418473, compound

Product 1

HCID 49806218HCID 49806218, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

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 (0.2 g, 0.5 mmol) in anhydrous diethyl ether (5 mL) at 0° C. was added a solution of allylmagnesium chloride in tetrahydrofuran (1.3 M, 2.16 mL, 4 mmol) dropwise. After stirring at 0° C. for 30 min, the reaction was quenched by adding saturated aqueous ammonium chloride solution (10 mL). The mixture was extracted with diethyl ether (2×50 mL), washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was re-crystallized from diethyl ether to afford 8,8-diallyl-9,10-dimethoxy-5,8-dihydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline (28 mg, 13%). LC/MS m/e calcd for C26H27NO4 (M+H)+: 418.51, observed: 418.3; 1H NMR (400 MHz, DMSO-d6) δ ppm 2.66-2.78 (m, 4 H) 2.94 (dd, J=15.41, 6.06 Hz, 2 H) 3.26 (t, J=5.43 Hz, 2 H) 3.77 (d, J=10.36 Hz, 6 H) 4.88 (d, J=10.36 Hz, 2 H) 4.98 (d, J=17.43 Hz, 2 H) 5.35 (s, 1 H) 5.66-5.78 (m, J=16.99, 10.29, 7.07, 6.82 Hz, 2 H) 5.98 (s, 2 H) 6.51 (d, J=8.34 Hz, 1 H) 6.72 (s, 1 H) 6.80 (d, J=8.34 Hz, 1 H) 7.15 (s, 1 H).

Workup

  1. customthe reaction was quenched
  2. additionby adding saturated aqueous ammonium chloride solution (10 mL)
  3. extractionThe mixture was extracted with diethyl ether (2×50 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-439daea8828a4d778683cba1e19facd6
Source dataset
uspto-grants-2012_09
Patent number
US08258149B2

Reaction notes

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