Sulfuric Acid → 6-Bromo-8-methylquinolin-2(1H)-one

HRID 568386Notes

Reaction equation

HRID 568386 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:15])/[CH:10]=[CH:11]/OCC)=[C:4]([CH3:16])[CH:3]=1.S(=O)(=O)(O)O>>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[C:4]([CH3:16])[CH:3]=1)[NH:8][C:9](=[O:15])[CH:10]=[CH:11]2

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 14221021Trans-N-(4-bromo-2-methylphenyl)-3-ethoxypropenamide

Product 1

HCID 138361836-Bromo-8-methylquinolin-2(1H)-one

Procedure

Trans-N-(4-bromo-2-methylphenyl)-3-ethoxypropenamide (2.0 g) was added portionwise with stirring to 98% sulphuric acid (15 cm3) at room temperature. After 16 hours the solution was poured onto ice (100 cm3) and the resulting precipitate was filtered off and dried (1.5 g). Recrystallisation from ethyl acetate-methanol afforded 6-bromo-8-methyl-2-(1H)-quinolone, m.p. 272°-274°.

Workup

  1. additionAfter 16 hours the solution was poured onto ice (100 cm3)
  2. filtrationthe resulting precipitate was filtered off
  3. customdried (1.5 g)
  4. customRecrystallisation from ethyl acetate-methanol

Sources & evidence

ORD record
ord-6044856d9abf4673b1648f563919d97b
Source dataset
uspto-grants-1988_03
Patent number
US04728653

Reaction notes

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