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

HRID 568356Notes

Reaction equation

HRID 568356 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-2f35b15b5b12442eafa8bca4cdd5cade
Source dataset
uspto-grants-1988_03
Patent number
US04728654

Reaction notes

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