Hydrogen Bromide → 2,3-Dihydro-1H-isoindol-4-ol hydrobromide

HRID 424117Notes

Reaction equation

HRID 424117 reaction equation
C[O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][NH:6][CH2:7]2.[BrH:12]>>[BrH:12].[OH:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][NH:6][CH2:7]2

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 147958644-methoxy-2,3-dihydro-1H-isoindole

Product 1

HCID 198284942,3-Dihydro-1H-isoindol-4-ol hydrobromideYield 78%

Procedure

4-Methoxyisoindoline (4.4 g, 29.53 mmol) in 48% aqueous hydrobromic acid (50 ml) was stirred and held at reflux for 16 hours. Upon cooling to room temperature the solvent was removed in vacuo to afford 4-hydroxyisoindoline hydrobromide (5.0 g, 78%) as a pale orange solid. 1H NMR (DMSO-d6) 9.95 (1H, br s), 9.37 (2H, br s), 7.19 (1H, t), 6.84 (1H, d), 6.80 (1H, d), 4.48 (2H, t), 4.40 (2H, t). MS: [M+H]+ 136.

Workup

  1. temperatureat reflux for 16 hours
  2. customwas removed in vacuo

Sources & evidence

ORD record
ord-16aff7a4d69f402aab752ce49c15227d
Source dataset
uspto-grants-2012_01
Patent number
US08101648B2

Reaction notes

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