Chloride → HCID 49806215, compound

HRID 2381205Notes

Reaction equation

HRID 2381205 reaction equation
ClC1[NH+:11]2[CH2:12][CH2:13][C:14]3[C:19]([C:10]2=[C:9]([CH3:23])[C:8]2[CH:7]=[CH:6][C:5]([O:24][CH3:25])=C(OC)C1=2)=[CH:18][C:17]1[O:20][CH2:21][O:22][C:16]=1[CH:15]=3.[Cl-].C[Mg]Cl.O1C[CH2:35][CH2:34][CH2:33]1.[CH2:37]([O:39][CH2:40][CH3:41])C>>[CH3:37][O:39][C:40]1[C:41]2[C:34]([CH3:35])([CH3:33])[N:11]3[CH2:12][CH2:13][C:14]4[C:19]([C:10]3=[C:9]([CH3:23])[C:8]=2[CH:7]=[CH:6][C:5]=1[O:24][CH3:25])=[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 86647494HCID 86647494, compoundHCID 178418332HCID 178418332, compound

Product 1

HCID 49806215HCID 49806215, compoundYield 9%

Conditions

Temperature
0 °C

Procedure

To a suspension of 8-chloro-9,10-dimethoxy-13-methyl-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ylium; chloride (970 mg, 2.3 mmol) in anhydrous diethyl ether (150 mL) at 0° C. was added a solution of methylmagnesium chloride in tetrahydrofuran (3 M, 15 mL, 45 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-8,8,13-trimethyl-5,8-dihydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline (80 mg, 9%). LC/MS m/e calcd for C23H25NO4 (M+H)+: 380.46, observed: 380.1; 1H NMR (400 MHz, DMSO-d6) δ ppm 1.56 (s, 6 H) 2.12 (s, 3 H) 2.63 (t, J=5.18 Hz, 2 H) 3.16 (t, J=5.31 Hz, 2 H) 3.73 (s, 3 H) 3.79 (s, 3 H) 6.01 (s, 2 H) 6.81 (s, 1 H) 6.86-6.93 (m, 2 H) 6.98 (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-10588d09329848ec94836ec0e302db41
Source dataset
uspto-grants-2012_09
Patent number
US08258149B2

Reaction notes

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