Ethyl Acetate → HCID 86681660, compound

HRID 571246Notes

Reaction equation

HRID 571246 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[N+:12]([O-])=O)[C:8](=[O:15])[N:7]([CH2:16][C:17]([O:19][CH3:20])=[O:18])[C:6]2=[O:21].C(OCC)(=O)C>CO.C(Cl)Cl.[Pd]>[NH2:12][C:11]1[CH:10]=[C:9]2[C:5](=[CH:4][C:3]=1[O:2][CH3:1])[C:6](=[O:21])[N:7]([CH2:16][C:17]([O:19][CH3:20])=[O:18])[C:8]2=[O:15]

Participants

6

Reactant 2

HCID 8857Ethyl AcetateHCID 86681658HCID 86681658, compound

Product 1

HCID 86681660HCID 86681660, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of methyl 2-(5-methoxy-6-nitro-1,3-dioxoisoindolin-2-yl)acetate (0.225 g, 0.765 mmol) and 10% w/w Pd/C (a catalytic amount) in MeOH (20 ml) and ethyl acetate (10 ml) was hydrogenated in a Parr apparatus at 15 psi for 1 hour. The mixture was diluted with DCM till complete dissolution of the yellow precipitate, the catalyst was filtered off and the filtrate was evaporate to dryness affording methyl 2-(5-amino-6-methoxy-1,3-dioxoisoindolin-2-yl)acetate (0.202 g, 0.764 mmol, 100% yield). MS/ESI+ 265.0 [MH]+.

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporate to dryness

Sources & evidence

ORD record
ord-cc10e411202b4159b462710b25400804
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

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