Methanol → 2-Benzyloxy-6-methoxy-benzo[de]-isoquinoline-1,3-dione

HRID 567007Notes

Reaction equation

HRID 567007 reaction equation
[CH2:1]([O:8][N:9]1[C:18](=[O:19])[C:17]2[CH:20]=[CH:21][C:22](Br)=[C:15]3[C:16]=2[C:11](=[CH:12][CH:13]=[CH:14]3)[C:10]1=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:27][OH:28]>>[CH2:1]([O:8][N:9]1[C:18](=[O:19])[C:17]2[CH:20]=[CH:21][C:22]([O:28][CH3:27])=[C:15]3[C:16]=2[C:11](=[CH:12][CH:13]=[CH:14]3)[C:10]1=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24758Sodium hydrideHCID 226240382-Benzyloxy-6-bromo-benzo[de]isoquinoline-1,3-dione

Product 1

HCID 226239102-Benzyloxy-6-methoxy-benzo[de]-isoquinoline-1,3-dione

Procedure

2-Benzyloxy-6-bromo-benzo[de]isoquinoline-1,3-dione (3.2 g, 8.4 mmol, from Example M) was added to a solution of sodium hydride (0.5 g, 12.5 mmol) in methanol (100 mL). The mixture was refluxed for 8 hours and concentrated in vacuo. The solid residue was dissolved in water and acidified with concentrated HCl to pH 4. The resulting precipitate was filtered, washed with water, and dried to give 0.8 g of 2-benzyloxy-6-methoxy-benzo[de]-isoquinoline-1,3-dione. The hydrogenation of 2-benzyloxy-6-methoxy-benzo[de]isoquinoline-1,3-dione (0.6 g) in the presence of Pd/C (10%) in DMA (20 mL) afforded 0.2 g of the title compound, mp 267-269° C.;

Workup

  1. temperatureThe mixture was refluxed for 8 hours
  2. concentrationconcentrated in vacuo
  3. dissolutionThe solid residue was dissolved in water
  4. filtrationThe resulting precipitate was filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-c44bdea91669497a8392154052a9bdd5
Source dataset
uspto-grants-2001_01
Patent number
US06177423B1

Reaction notes

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