Hydrochloric Acid → 5-Nitroisoindoline

HRID 1726221Notes

Reaction equation

HRID 1726221 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=O)[NH:10][C:8](=O)[C:7]2=[CH:13][CH:14]=1)([O-:3])=[O:2].B.C1COCC1.Cl>C1COCC1>[N+:1]([C:4]1[CH:5]=[C:6]2[C:7](=[CH:13][CH:14]=1)[CH2:8][NH:10][CH2:11]2)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 69694-NitrophthalimideHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 64244695-NitroisoindolineYield 28%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Nitrophthalimide (8.0 g, 41.6 mmol) in THF (10 mL) was reduced with BH3-THF (1.0M in THF, 111 mL, 111 mmol) at reflux and treated with 6N HCl to afford 5-nitro-2,3-dihydro-1H-isoindole (1.89 g, 28%) after work-up and purification.

Workup

  1. temperatureat reflux

Sources & evidence

ORD record
ord-d362d64a41eb4dc9bd5026f355f3e42b
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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