tert-butyl 5-nitro-2,3-dihydro-1H-isoindole-2-carboxylate → tert-butyl 5-amino-2,3-dihydro-1H-isoindole-2-carboxylate

HRID 1394185Notes

Reaction equation

HRID 1394185 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([N+:17]([O-])=O)[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([NH2:17])[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 16450129tert-butyl 5-nitro-2,3-dihydro-1H-isoindole-2-carboxylate

Product 1

HCID 22591361tert-butyl 5-amino-2,3-dihydro-1H-isoindole-2-carboxylateYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The product of Step 2 (3.5 g, 13.25 mmol) was dissolved in ethanol (200 ml) and treated with 10 wt % Palladium on charcoal (1 g), and stirred under 1 atm of H2 for 16 hours. The reaction was filtered and evaporated in vacuo to afford the title compound (3.01 g, 96%); MS (ES+), m/e 235 [M+H]+.

Workup

  1. filtrationThe reaction was filtered
  2. customevaporated in vacuo

Sources & evidence

ORD record
ord-f857730093cf4b9e8b6ec53ec2804796
Source dataset
uspto-grants-2008_03
Patent number
US07348339B2

Reaction notes

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