HCID 67417282, compound → HCID 67416470, compound

HRID 1727439Notes

Reaction equation

HRID 1727439 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[C:6](=[O:28])[N:7]([CH:14]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH2:26][CH3:27])[CH:18]=1)[C:15]#[N:16])[C:8]2=[O:13])([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[C:6](=[O:28])[N:7]([CH:14]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH2:26][CH3:27])[CH:18]=1)[C:15]#[N:16])[C:8]2=[O:13]

Participants

4

Reactant 1

HCID 67417282HCID 67417282, compound

Product 1

HCID 67416470HCID 67416470, compoundYield 120.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2-(nitro-1,3-dioxoisoindolin-2-yl)-2-(3-ethoxy-4-methoxyphenyl)ethanenitrile (3.9 g, 7.8 mmol) and 10% Pd/C (0.6 g) in methanol (150 mL) was hydrogenated at 50 psi for 3 hours. The mixture was filtered through celite, and the celite was washed with methylene chloride. The filtrate was concentrated and the residue was purified by chromatography (SiO2, CH2Cl2:CH3OH 95:5) to give 3.3 g (91%) of 2-(4-amino-1,3-dioxoisoindolin-2-yl)-2-(3-ethoxy-4-methoxyphenyl)ethanenitrile; 1H NMR (DMSO-d6) δ 7.50-7.43 (dd, J=7.3 and 8.3 Hz, 1H), 7.03-6.91 (m, 5H), 6.55 (s, 2H), 5.55-5.48 (dd, J=6.6 and 9.9 Hz, 1H), 3.99 (q, J=7.0 Hz, 2H), 3.72 (s, 3H), 3.76-3.48 (m, 2H), 1.31 (t, J=7 Hz, 3H); 13C NMR (DMSO-d6) δ 168.81, 167.59, 148.88 146.82, 135.55, 131.56, 129.70, 121.86, 121.80, 119.27, 118.26, 112.10, 111.82, 111.06, 63.82, 55.48, 49.46, 20.54, 14.61.

Workup

  1. filtrationThe mixture was filtered through celite
  2. washthe celite was washed with methylene chloride
  3. concentrationThe filtrate was concentrated
  4. customthe residue was purified by chromatography (SiO2, CH2Cl2:CH3OH 95:5)

Sources & evidence

ORD record
ord-22fb9202b50248afad61d8a038e19f3d
Source dataset
uspto-grants-2009_02
Patent number
US07495112B2

Reaction notes

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