Bromide ion → HCID 59574873, compound

HRID 2381209Notes

Reaction equation

HRID 2381209 reaction equation
[CH2:1]([C:8]1[C:9]2[CH:10]=[CH:11][C:12]([O:31][CH3:32])=[C:13]([O:29][CH3:30])[C:14]=2[CH2:15][NH+:16]2[CH2:25][CH2:24][C:23]3[C:18](=[CH:19][C:20]4[O:28][CH2:27][O:26][C:21]=4[CH:22]=3)[C:17]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br-].[OH-:34].[Na+]>O>[CH2:1]([C:8]1[C:9]2[CH:10]=[CH:11][C:12]([O:31][CH3:32])=[C:13]([O:29][CH3:30])[C:14]=2[C:15](=[O:34])[N:16]2[CH2:25][CH2:24][C:23]3[C:18](=[CH:19][C:20]4[O:28][CH2:27][O:26][C:21]=4[CH:22]=3)[C:17]=12)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 259Bromide ionHCID 14798Sodium HydroxideHCID 86647496HCID 86647496, compound

Product 1

HCID 59574873HCID 59574873, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 13-benzyl-9,10-dimethoxy-5,6-dihydro[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ylium; bromide (0.9 g, 1.8 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. The residue was re-crystallized from ethanol to afford 13-benzyl-9,10-dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-8-one (180 mg. 22%) LC/MS m/e calcd for C27H23NO5 (M+H)+: 442.49, observed: 442.1.

Workup

  1. customThe precipitate was collected
  2. additiontreated with hot 3% hydrochloric acid
  3. customThe residue was re-crystallized from ethanol

Sources & evidence

ORD record
ord-3d2670486c36406bb81caf3e7057c986
Source dataset
uspto-grants-2012_09
Patent number
US08258149B2

Reaction notes

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