(5-Nitro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-acetic acid ethyl ester → (5-Amino-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-acetic acid ethyl ester

HRID 523812

Reaction equation

HRID 523812 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH2:5][N:6]1[C:14](=[O:15])[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([N+:16]([O-])=O)[CH:12]=2)[C:7]1=[O:19])[CH3:2]>C(O)(=O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:20])[CH2:5][N:6]1[C:14](=[O:15])[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([NH2:16])[CH:12]=2)[C:7]1=[O:19])[CH3:2]

Participants

4

Reactant 1

HCID 784823(5-Nitro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-acetic acid ethyl ester

Product 1

HCID 13848438(5-Amino-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-acetic acid ethyl esterYield 78.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

10% Palladium/C (50% wet) solid (2.0 g) was added to a solution mixture of (5-nitro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-acetic acid ethyl ester (10.0 g) in glacial acetic acid (150 ml). Stirred vigorously under H2 (balloon pressure) at room temperature overnight (18 h). Catalyst was filtered off through a pad of celite and rinsed with methylene chloride. Filtrate was concentrated to give the title compound (7.0 g). 1H NMR (200 MHz, CDCl3) δ 7.59 (d, J=8.2 Hz, 1H), 7.02 (d, J=2.0 Hz, 1H), 6.81 (dd, J=8.2, 2.0 Hz, 1H), 4.38 (br S, 2H), 4.36 (s, 2H), 4.20 (q, J=7.0 Hz, 2H), 1.27 (t, J=7.0 Hz, 3H).

Workup

  1. filtrationCatalyst was filtered off through a pad of celite
  2. washrinsed with methylene chloride
  3. concentrationFiltrate was concentrated

Sources & evidence

ORD record
ord-a8e61d94d5114bf683bf45bb285f28ea
Source dataset
uspto-grants-2016_05
Patent number
US09339527B2

Linked notes

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