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

HRID 2381207Notes

Reaction equation

HRID 2381207 reaction equation
[CH2:1]([C:3]1[C:4]2[CH:5]=[CH:6][C:7]([O:26][CH3:27])=[C:8]([O:24][CH3:25])[C:9]=2[CH2:10][NH+:11]2[CH2:20][CH2:19][C:18]3[C:13](=[CH:14][C:15]4[O:23][CH2:22][O:21][C:16]=4[CH:17]=3)[C:12]=12)[CH3:2].[I-].[OH-:29].[Na+]>O>[CH2:1]([C:3]1[C:4]2[CH:5]=[CH:6][C:7]([O:26][CH3:27])=[C:8]([O:24][CH3:25])[C:9]=2[C:10](=[O:29])[N:11]2[CH2:20][CH2:19][C:18]3[C:13](=[CH:14][C:15]4[O:23][CH2:22][O:21][C:16]=4[CH:17]=3)[C:12]=12)[CH3:2]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 30165Iodide IonHCID 8664749213-Ethyl-9,10-dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ylium

Product 1

HCID 5957487713-Ethyl-9,10-dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-8-oneYield 12%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 13-ethyl-9,10-dimethoxy-5,6-dihydro[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ylium; iodide (1.1 g, 2.2 mmol) and 30% sodium hydroxide in water (150 mL) was refluxed for 56 h. The precipitate formed was collected and treated with hot 3% hydrochloric acid. The precipitate was collected and re-crystallized from ethanol to afford 13-ethyl-9,10-dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-8-one (100 mg. 12%).

Workup

  1. customThe precipitate formed
  2. customwas collected
  3. additiontreated with hot 3% hydrochloric acid
  4. customThe precipitate was collected
  5. customre-crystallized from ethanol

Sources & evidence

ORD record
ord-fee380d1cc3f4509aafa7c4e743d2ae7
Source dataset
uspto-grants-2012_09
Patent number
US08258149B2

Reaction notes

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