Phenylacetic Acid → HCID 19900409, compound

HRID 1029486Notes

Reaction equation

HRID 1029486 reaction equation
Cl[CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[N:15][C:16]([Cl:22])=[CH:17][CH:18]=2)[N:13]=1.[C:23]1([CH2:29][C:30]([OH:32])=[O:31])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.N12CCCN=C1CCCCC2>CN(C)C=O>[C:23]1([CH2:29][C:30]([O:32][CH:2]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:4](=[O:11])[N:3]2[C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[N:15][C:16]([Cl:22])=[CH:17][CH:18]=3)[N:13]=2)=[O:31])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 999Phenylacetic AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 141824043-Chloro-2-(7-chloro-1,8-naphthyridin-2-yl)-1-isoindolinone

Product 1

HCID 19900409HCID 19900409, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The procedure is as in Example 1, but starting with 3-chloro-2-(7-chloro-1,8-naphthyridin-2-yl)-1-isoindolinone (4.95 g) in anhydrous dimethylformamide (60 cc), phenylacetic acid (2.05 g) and 1,8-diazabicyclo[5.4.0]-undec-7-ene (2.25 g). After recrystallization in ethyl acetate, 2-(7-chloro-1,8-naphthyridin-2-yl)-3-oxo-1-isoindolinyl phenylacetate (4.4 g), m.p. 222°-224° C., is obtained.

Workup

  1. customAfter recrystallization in ethyl acetate

Sources & evidence

ORD record
ord-402ca640bef442518131b0c02bd40a0d
Source dataset
uspto-grants-1992_04
Patent number
US05102890

Reaction notes

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