N-(4-bromo-2-methylphenyl)-3-oxobutanamide → 6-Bromo-4,8-dimethylquinolin-2(1H)-one

HRID 986011Notes

Reaction equation

HRID 986011 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:14])[CH2:10][C:11]([CH3:13])=O)=[C:4]([CH3:15])[CH:3]=1>S(=O)(=O)(O)O>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[C:4]([CH3:15])[CH:3]=1)[NH:8][C:9](=[O:14])[CH:10]=[C:11]2[CH3:13]

Participants

3

Reactant 1

HCID 4100579N-(4-bromo-2-methylphenyl)-3-oxobutanamide

Product 1

HCID 145703026-Bromo-4,8-dimethylquinolin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

N-[4-Bromo-2-methylphenyl]-acetoacetamide (18 g) was heated for 5 hours with stirring in 98% sulphuric acid (50 cm3) at 100°. The cooled mixture was then poured onto ice (200 g), the solid was filtered off and dried in vacuo at 100° for 2 hours to give the crude product (15.0 g). A small portion (1.5 g) of this material was recrystallised from ethyl acetate/methanol to afford 6-bromo-4,8-dimethyl-2-(1H)-quinolone, m.p. >300° (1.1 g).

Workup

  1. additionThe cooled mixture was then poured onto ice (200 g)
  2. filtrationthe solid was filtered off
  3. customdried in vacuo at 100° for 2 hours
  4. customto give the crude product (15.0 g)
  5. customA small portion (1.5 g) of this material was recrystallised from ethyl acetate/methanol

Sources & evidence

ORD record
ord-b7d54538928d434494151a06f531683c
Source dataset
uspto-grants-1987_12
Patent number
US04710507

Reaction notes

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