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

HRID 1199532Notes

Reaction equation

HRID 1199532 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-4f07a46580394ddf972d9323390c58e2
Source dataset
uspto-grants-1990_02
Patent number
US04900839

Reaction notes

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