HCID 12110002, compound → HCID 12110003, compound

HRID 433292Notes

Reaction equation

HRID 433292 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:28])[N:5]([CH:12]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH2:26][CH3:27])[CH:18]=1)[CH2:13][CH:14]([OH:16])[CH3:15])[C:6]2=[O:11].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl>[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:28])[N:5]([CH:12]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH2:26][CH3:27])[CH:18]=1)[CH2:13][C:14](=[O:16])[CH3:15])[C:6]2=[O:11]

Participants

4

Reactant 2

HCID 12110002HCID 12110002, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 12110003HCID 12110003, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-amino-2-[1-(3-ethoxy-4-methoxyphenyl)-3-hydroxybutyl]isoindoline-1,3-dione (0.7 g, 1.82 mmol), pyridinium chlorochromate (0.79 g, 3.64 mmol) and Celite (0.6 g) in methylene chloride (40 mL) was stirred at room temperature for 4 hours. The mixture was filtered through celite and the filtrate was washed with water, brine, dried and concentrated. The residue was purified by chromatography (silica gel, methylene chloride:ethyl acetate 95:5) to give 4-amino-2-[1-(3-ethoxy-4-methoxyphenyl)-3-oxobutyl]isoindoline-1,3-dione as a white solid (0.49 g, 71%); 1H NMR (CDCl3) δ7.38-7.31 (t, J=7.3 Hz, 1H), 7.08-7.05 (m, 3H), 6.81-6.77 (m, 2H), 5.74-5.67 (dd, J=5.9 and 9.4 Hz, 1H), 5.20 (s, 2H), 4.11 (q, J=7.0 Hz, 2H), 3.98-3.87 (dd, J=9.5 and 17.8 Hz, 1H), 3.83 (s, 3H), 3.33-3.23 (dd, J=5.6 and 17.7 Hz, 1H), 2.18-(s, 3H), 1.44 (t, J-6.9 Hz, 3H).

Workup

  1. filtrationThe mixture was filtered through celite
  2. washthe filtrate was washed with water, brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography (silica gel, methylene chloride:ethyl acetate 95:5)

Sources & evidence

ORD record
ord-930408508caa47b1aef4c8cf039477ab
Source dataset
uspto-grants-2003_12
Patent number
US06667316B1

Reaction notes

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