Sodium Hydroxide → 9,10-Dimethoxy-13-methyl-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-8-one

HRID 2381204Notes

Reaction equation

HRID 2381204 reaction equation
[CH3:1][O:2][C:3]1[C:23]2[CH2:22][NH+:10]3[CH2:11][CH2:12][C:13]4[C:18]([C:9]3=[C:8]([CH3:24])[C:7]=2[CH:6]=[CH:5][C:4]=1[O:25][CH3:26])=[CH:17][C:16]1[O:19][CH2:20][O:21][C:15]=1[CH:14]=4.[I-].[OH-:28].[Na+]>O>[CH3:1][O:2][C:3]1[C:23]2[C:22](=[O:28])[N:10]3[CH2:11][CH2:12][C:13]4[C:18]([C:9]3=[C:8]([CH3:24])[C:7]=2[CH:6]=[CH:5][C:4]=1[O:25][CH3:26])=[CH:17][C:16]1[O:19][CH2:20][O:21][C:15]=1[CH:14]=4

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 30165Iodide IonHCID 866474919,10-Dimethoxy-13-methyl-5,6-dihydro[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ylium

Product 1

HCID 595748749,10-Dimethoxy-13-methyl-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-8-oneYield 20%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 9,10-dimethoxy-13-methyl-5,6-dihydro[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ylium; iodide (0.95 g, 2.0 mmol) and 30% sodium hydroxide in water (150 mL) was refluxed for 16 h. The precipitate was collected and treated with hot 3% hydrochloric acid. Purification by flash silica gel chromatography (silica gel from QingDao, 100-200 mesh, glass column from Shanghai SD company) (50% dichloromethane/ethyl acetate) afforded 9,10-dimethoxy-13-methyl-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-8-one (150 mg. 20%) LC/MS m/e calcd for C21H19NO5 (M+H)+: 366.69, observed: 366.1; 1H NMR (400 MHz, DMSO-d6) δ ppm 2.46 (s, 3 H) 2.80 (t, J=5.56 Hz, 2 H) 3.78 (s, 3 H) 3.90 (s, 3 H) 3.96-4.07 (m, 2 H) 6.09 (s, 2 H) 7.00 (s, 1 H) 7.16 (s, 1 H) 7.54-7.61 (m, 2 H).

Workup

  1. customThe precipitate was collected
  2. additiontreated with hot 3% hydrochloric acid
  3. customPurification by flash silica gel chromatography (silica gel from QingDao, 100-200 mesh, glass column from Shanghai SD company) (50% dichloromethane/ethyl acetate)

Sources & evidence

ORD record
ord-0f601c868c4b430ebac4c7b49f79282c
Source dataset
uspto-grants-2012_09
Patent number
US08258149B2

Reaction notes

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