2-Benzyloxy-5-cyano-6-(pyrrolidin-1-yl)-benzo[de]isoquinoline-1,3-dione → 5-Cyano-2-hydroxy-6-(pyrrolidin-1-yl)-benzo[de]isoquinoline-1,3-dione

HRID 567030Notes

Reaction equation

HRID 567030 reaction equation
C([O:8][N:9]1[C:18](=[O:19])[C:17]2[CH:20]=[C:21]([C:28]#[N:29])[C:22]([N:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)=[C:15]3[C:16]=2[C:11](=[CH:12][CH:13]=[CH:14]3)[C:10]1=[O:30])C1C=CC=CC=1.FC(F)(F)C([O-])=O.FC(F)(F)C([O-])=O.FC(F)(F)C([O-])=O.[B+3]>C(O)(C(F)(F)F)=O>[C:28]([C:21]1[C:22]([N:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)=[C:15]2[CH:14]=[CH:13][CH:12]=[C:11]3[C:16]2=[C:17]([CH:20]=1)[C:18](=[O:19])[N:9]([OH:8])[C:10]3=[O:30])#[N:29]

Participants

4

Reactant 2

HCID 226239112-Benzyloxy-5-cyano-6-(pyrrolidin-1-yl)-benzo[de]isoquinoline-1,3-dioneHCID 178525683HCID 178525683, compound

Product 1

HCID 226240555-Cyano-2-hydroxy-6-(pyrrolidin-1-yl)-benzo[de]isoquinoline-1,3-dioneYield 69%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Following the procedure of Example 52, 2-benzyloxy-5-cyano-6-(pyrrolidin)-1-yl)-benzo[de]isoquinoline-1,3-dione (0.15 g, 0.33 mmol, from Example B2) and a 1.0 M solution of boron tris(trifluoroacetate) in TFA (2 mL) was reacted to give 0.070 g of the title compound, mp 247-248° C.

Sources & evidence

ORD record
ord-62ba51488ba04078baf060ef89eb0113
Source dataset
uspto-grants-2001_01
Patent number
US06177423B1

Reaction notes

Loading…