HCID 8820864, compound → HCID 86681697, compound

HRID 571292Notes

Reaction equation

HRID 571292 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[N:8]([CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:7]2=[O:22])([O-])=O>C(OCC)(=O)C.CO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[N:8]([CH2:14][C:15]([O:17][C:18]([CH3:20])([CH3:19])[CH3:21])=[O:16])[C:7]2=[O:22]

Participants

5

Reactant 1

HCID 8820864HCID 8820864, compound

Product 1

HCID 86681697HCID 86681697, compoundYield 99%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl 2-(5-nitro-1,3-dioxoisoindolin-2-yl)acetate (15.7 g, 51.3 mmol) in a mixture of ethyl acetate (400 ml) and MeOH (200 ml), 10% w/w Pd/C (0.900 g) was added, and the mixture was hydrogenated in a Parr apparatus at 30 psi for 2 hours. The catalyst was filtered off, and the filtrate was evaporated to dryness affording tert-butyl 2-(5-amino-1,3-dioxoisoindolin-2-yl)acetate (14 g, 50.7 mmol, 99% yield, MS/ESI+ 276.9 [MH]+). This product was used in the following step without any further purification.

Workup

  1. additionwas added
  2. filtrationThe catalyst was filtered off
  3. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-11f5a53ffeae4f98a7b5c6882b3fd119
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

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