2-(4-Nitro-1,3-dioxoisoindolin-2-yl)-4-carbamoylbutanoic acid → 2H-Isoindole-2-acetic acid, 4-amino-alpha-(3-amino-3-oxopropyl)-1,3-dihydro-1,3-dioxo-

HRID 844221Notes

Reaction equation

HRID 844221 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[C:6](=[O:23])[N:7]([CH:14]([CH2:18][CH2:19][C:20](=[O:22])[NH2:21])[C:15]([OH:17])=[O:16])[C:8]2=[O:13])([O-])=O.[H][H]>CN(C)C=O.[Pd]>[NH2:1][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[C:6](=[O:23])[N:7]([CH:14]([CH2:18][CH2:19][C:20](=[O:22])[NH2:21])[C:15]([OH:17])=[O:16])[C:8]2=[O:13]

Participants

5

Reactant 2

HCID 155498382-(4-Nitro-1,3-dioxoisoindolin-2-yl)-4-carbamoylbutanoic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 155498392H-Isoindole-2-acetic acid, 4-amino-alpha-(3-amino-3-oxopropyl)-1,3-dihydro-1,3-dioxo-

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-(4-nitro-1,3-dioxoisoindolin-2-yl)-4-carbamoylbutanoic acid (5 mmol) and 10% Pd/C (250 mg) in dimethylformamide is hydrogenated under 60 psi of hydrogen in a Parr Type Shaker to afford 2-(4-amino-1,3-dioxoisoindolin-2-yl)-4-carbamoylbutanoic acid.

Sources & evidence

ORD record
ord-99ae6b197ac642b6899a5674131adc78
Source dataset
uspto-grants-2002_04
Patent number
US06380239B1

Reaction notes

Loading…