Potassium Iodide → HCID 22623970, compound

HRID 279004Notes

Reaction equation

HRID 279004 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.Br[CH:26]([CH3:30])[C:27]([OH:29])=[O:28].C(=O)([O-])[O-].[K+].[K+].[I-].[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][CH2:26][C:27]([OH:29])=[O:28])[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

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 117292-Bromopropionic acidHCID 22624014HCID 22624014, compound

Product 1

HCID 22623970HCID 22623970, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-Benzyloxy-5-hydroxy-benzo[de]isoquinoline-1,3-dione (1.1 g, 3.5 mmol) and 2-bromopropionic acid (1.2 g, 7.8 mmol) were reacted in acetone (300 mL) in presence of potassium carbonate (2.3 g, 5.1 mmol) and potassium iodide (0.1 g, 0.6 mmol), following the procedure of Example 22 to give 1.1 g of 2-benzyloxy-5-(2-carboxy-ethoxy)-benzo[de]isoquinoline-1,3-dione. The hydrogenation of 2-benzyloxy-5-(2-carboxy-ethoxy)-benzo[de]isoquinoline-1,3-dione (1.1 g) in the presence of 10% Pd/C (0.5 g) in DMA (20 mL) afforded 0.3 g of the title compound, mp 236-239° C.;

Sources & evidence

ORD record
ord-0228dba098d34a51859df3cd7a70e588
Source dataset
uspto-grants-2002_03
Patent number
US06362181B1

Reaction notes

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