1-(4-Nitro-1-oxoisoindolin-2-yl)propane-1,3-dicarboxylic acid dibenzyl ester → 2-(4-Amino-1-oxoisoindolin-2-yl)pentanedioic acid

HRID 844227Notes

Reaction equation

HRID 844227 reaction equation
C([O:8][C:9]([CH:11]([N:24]1[CH2:32][C:31]2[C:26](=[CH:27][CH:28]=[CH:29][C:30]=2[N+:33]([O-])=O)[C:25]1=[O:36])[CH2:12][CH2:13][C:14]([O:16]CC1C=CC=CC=1)=[O:15])=[O:10])C1C=CC=CC=1.[H][H]>[Pd].CO>[NH2:33][C:30]1[CH:29]=[CH:28][CH:27]=[C:26]2[C:31]=1[CH2:32][N:24]([CH:11]([C:9]([OH:10])=[O:8])[CH2:12][CH2:13][C:14]([OH:16])=[O:15])[C:25]2=[O:36]

Participants

5

Reactant 2

HCID 155498421-(4-Nitro-1-oxoisoindolin-2-yl)propane-1,3-dicarboxylic acid dibenzyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 155498432-(4-Amino-1-oxoisoindolin-2-yl)pentanedioic acidYield 81.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1-(4-nitro-1-oxoisoindolin-2-yl)propane-1,3-dicarboxylic acid dibenzyl ester (2.6 g, 5.3 mmol), 10%Pd/C (0.26 g) and methanol (50 mL) is hydrogenated at 50 psi of hydrogen for 6 hours. The mixture is filtered through celite and the celite pad is washed with methanol (50 mL). The filtrate is concentrated in vacuo to give 1-(4-amino-1-oxoisoindolin-2-yl)propane-1,3-dicarboxylic acid (1.2 g, 81%); mp 183-185° C.; 1H NMR (DMSO-d6) δ7.17 (t, J=7.6 Hz, 1H), 6.89 (d, J=7.3 Hz, 1H), 6.79 (d, J=7.8 Hz, 1H), 5.50 (b, 2H), 4.82-4.77 (m, 1H), 4.23 (s, 2H), 2.31-1.98 (m, 4H); 13C NMR (DMSO-d6) δ173.46, 172.28, 168.98, 143.58, 132.21, 128.73, 125.65, 116.24, 110.34, 52.83, 45.19, 30.32, 24.42; Anal. Calcd. For C13H14N2O5; C, 56.11; H, 5.07; N, 10.07. Found: C, 55.95; H, 5.37; N, 9.73.

Workup

  1. filtrationThe mixture is filtered through celite
  2. washthe celite pad is washed with methanol (50 mL)
  3. concentrationThe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-3d4538817e4a4c02a9ad3af05c67fc37
Source dataset
uspto-grants-2002_04
Patent number
US06380239B1

Reaction notes

Loading…