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 HCl

Procedure

5-Methoxy-2,3-dihydro-1H-isoindole (28.7 g) was dissolved in 48% hydrobromic acid (620 ml) and the mixture heated under reflux for 2 h, then cooled and evaporated to give 5-hydroxy-2,3-dihydro-1H-isoindole hydrobromide (29.5 g) as a brown solid. To the above hydrobromide salt (29.5 g) in tetrahydrofuran (215 ml) and water (215 ml) at 0° C. was added triethylamine (48 ml) followed by di-tert-butyl dicarbonate (33 g). The reaction was stirred for 18 h, then worked up as for Description 1 above and chromatographed on silica gel, to give the title compound (13.2 g, 29%) as a brown solid.

Workup

temperaturethe mixture heated
temperatureunder reflux for 2 h
temperaturecooled
customevaporated

Sources & evidence

ORD record: ord-a11314d5656c461ca690a290772da00a
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06521638B1

Reaction notes

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