Hydrogen Bromide → Isoindolin-5-ol HCl

Reaction equation

C[O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH2:8][NH:7][CH2:6]2.[BrH:12]>>[BrH:12].[OH:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH2:8][NH:7][CH2:6]2

Participants

Reactant 2

HCID 260Hydrogen Bromide

HCID 147958725-methoxy-2,3-dihydro-1H-isoindole

Product 1

HCID 18630974Isoindolin-5-ol HClYield 93%

Procedure

5-Methoxyisoindoline (8.34 g, 55.97 mmol) in 48% aqueous hydrobromic acid (100 ml) was stirred and held at reflux for 16 hours. Upon cooling to room temperature the solvent was removed in vacuo to afford 5-hydroxyisoindoline hydrobromide (11.32 g, 93%) as a tan solid. 1H NMR (DMSO-d6) 9.63 (1H, br s), 9.32 (2H, br s), 7.18 (1H, d), 6.79 (1H, d), 6.76 (1H, dd), 4.42 (2H, t), 4.38 (2H, t). MS: [M+H]+ 136.

Workup

temperatureat reflux for 16 hours
customwas removed in vacuo

Sources & evidence

ORD record: ord-0f83e415402a4867b7606ae249d93973
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08883790B2

Reaction notes

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