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

HRID 1919027Notes

Reaction equation

HRID 1919027 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[CH2:9][N:8]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:7]2)([O-])=O>[Pd].C(O)C>[NH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[CH2:9][N:8]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:7]2

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 99.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer was charged with tert-butyl 5-nitroisoindoline-2-carboxylate (650 mg, 2.5 mmol) and C2H5OH (50 mL). This solution was hydrogenated with Pd/C (160 mg) at room temperature for 15 h. It was then filtered and the filtrate was concentrated under reduced pressure to afford 231c as a yellow oil (585 mg, 99%), which was used in the next step without further purification. MS: [M+H]+ 179.

Workup

  1. customA 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer
  2. filtrationIt was then filtered
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c513b42e77624677bcf4b8c863d161cc
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

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