Potassium Carbonate → HCID 22624034, compound

HRID 279002Notes

Reaction equation

HRID 279002 reaction equation
[CH2:1]([O:8][N:9]1[C:18](=[O:19])[C:17]2[CH:20]=[C:21]([OH:23])[CH:22]=[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.[C:25]([O:28][CH2:29][CH2:30]Br)(=[O:27])[CH3:26].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:1]([O:8][N:9]1[C:18](=[O:19])[C:17]2[CH:20]=[C:21]([O:23][CH2:30][CH2:29][O:28][C:25](=[O:27])[CH3:26])[CH:22]=[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

5

Reactant 3

HCID 11430Potassium CarbonateHCID 135641-Acetoxy-2-bromoethaneHCID 22624014HCID 22624014, compound

Product 1

HCID 22624034HCID 22624034, compoundYield 95.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-Benzyloxy-5-hydroxy-benzo[de]isoquinoline-1,3-dione (1.0 g, 3.1 mmol), and 2-bromoethyl acetate (1.5 g, 9.0 mmol) were reacted in acetone (50 mL) in presence of potassium carbonate (0.7 g, 5.1 mmol) following the procedure of Example 22 to give 1.2 g of 2-benzyloxy-5-(2-acetoxy-ethoxy)-benzo[de]isoquinoline-1,3-dione. The hydrogenation of 2-benzyloxy-5-(2-acetoxy-ethoxy)-benzo[de]isoquinoline-1,3-dione (1.2 g) in the presence of 10% Pd/C (0.8 g) in ethyl acetate afforded 0.5 g of the title compound, mp 232-235° C.;

Sources & evidence

ORD record
ord-76edb339b45741da856432b6722152cb
Source dataset
uspto-grants-2002_03
Patent number
US06362181B1

Reaction notes

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