Sulfuric Acid → HCID 86723737, compound

HRID 577512Notes

Reaction equation

HRID 577512 reaction equation
OS(O)(=O)=O.[CH3:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[C:15](=[O:17])[NH:14][CH2:13][CH2:12]2.C1C(=O)N([Br:25])C(=O)C1>>[Br:25][C:8]1[C:7]([CH3:6])=[C:16]2[C:11]([CH2:12][CH2:13][NH:14][C:15]2=[O:17])=[CH:10][CH:9]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 67184N-bromobutanimideHCID 533993508-Methyl-3,4-dihydroisoquinolin-1(2H)-one

Product 1

HCID 86723737HCID 86723737, compoundYield 42.3%

Procedure

To cooled conc. H2SO4 (10 mL) was added 8-methyl-3,4-dihydroisoquinolin-1(2H)-one (76b, 1 g, 6.21 mmol) and the reaction mixture was stirred for 10 minutes. NBS (1.1 g, 6.21 mmol) was added and the reaction mixture stirred at 60° C. for 2 hours. The mixture was cooled to room temperature and poured into ice-water (30 mL) with stirring. The suspension was extracted with EtOAc (3×20 mL). The combined organic layers were washed with water (20 mL) and brine (20 mL), dried over Na2SO4, filtered, and concentrated in vacuum. The residue was purified by column chromatography (petroleum ether/EtOAc=1:1) to give 7-bromo-8-methyl-3,4-dihydroisoquinolin-1(2H)-one (76c, 0.63 g, 42%) as a white solid.

Workup

  1. stirringthe reaction mixture stirred at 60° C. for 2 hours
  2. stirringwith stirring
  3. extractionThe suspension was extracted with EtOAc (3×20 mL)
  4. washThe combined organic layers were washed with water (20 mL) and brine (20 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuum
  8. customThe residue was purified by column chromatography (petroleum ether/EtOAc=1:1)

Sources & evidence

ORD record
ord-be32c365beba4eafbe9e184b58691d70
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

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