Hydrochloric Acid → 8-Bromo-2,3-dihydroisoquinolin-4(1H)-one hcl

HRID 920240Notes

Reaction equation

HRID 920240 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH2:10][N:9](C(OC(C)(C)C)=O)[CH:8](C(OC)=O)[C:7]2=[O:23].[ClH:24].O>O1CCOCC1>[ClH:24].[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH2:10][NH:9][CH2:8][C:7]2=[O:23]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 962WaterHCID 89524864Methyl 2-Boc-8-bromo-4-oxo-1,2,3,4-tetrahydroisoquinoline-3-carboxylate

Product 1

HCID 895258908-Bromo-2,3-dihydroisoquinolin-4(1H)-one hcl

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a flask containing 2-tert-butyl 3-methyl 8-bromo-4-oxo-3,4-dihydroisoquinoline-2,3(1H)-dicarboxylate (24-1) (3.44 g, 8.95 mmol) (mixed with impurities) was added was added Dioxane (20 ml), then 5N HCl in H2O (20 ml, 100 mmol). The reaction mixture was then heated to 90 C in the hood overnight. Followed by LC/MS. The next morning another 20 mL of 5N HCl was added and the reaction mixture was heated to 110 C for 3 hours, then was concentrated. The resulting residue was triturated with DCM (hot, then cooled to room temperature) & filtered to yield 8-bromo-2,3-dihydroisoquinolin-4(1H)-one hydrochloride (24-2). HRMS [M+H]: calculated; 225.9862, observed; 225.9860.

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was then heated to 90 C in the hood overnight
  3. temperaturethe reaction mixture was heated to 110 C for 3 hours
  4. concentrationwas concentrated
  5. customThe resulting residue was triturated with DCM (hot,
  6. filtrationfiltered

Sources & evidence

ORD record
ord-f292d14bf7244c99b3498499fb91b189
Source dataset
uspto-grants-2016_03
Patent number
US09273040B2

Reaction notes

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