Hydrogen Bromide → 8-methyl-6-[4-hydroxylphenyl]-2-(1H)-quinolone

HRID 568344Notes

Reaction equation

HRID 568344 reaction equation
C[O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[C:6]([CH3:21])[CH:7]=[C:8]([C:13]3[CH:18]=[CH:17][C:16]([O:19]C)=[CH:15][CH:14]=3)[CH:9]=2)[N:4]=1.Br>O>[CH3:21][C:6]1[CH:7]=[C:8]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)[CH:9]=[C:10]2[C:5]=1[NH:4][C:3](=[O:2])[CH:12]=[CH:11]2

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 201504532-Methoxy-6-(4-methoxyphenyl)-8-methylquinoline

Product 1

HCID 201504468-methyl-6-[4-hydroxylphenyl]-2-(1H)-quinolone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-methoxy-8-methyl-6-[4-methoxyphenyl]quinoline (4.82 g) and 48% aqueous HBr (100 cm3) was heated under reflux for 6 hours. The cooled mixture was diluted with water (200 cm3), the solid filtered off, and dissolved in chloroform:methanol, 4:1 (500 cm3). The organic phase was washed with water (2×25 cm3), dried (MgS04) and evaporated in vacuo to give a solid which was recrystallised from propan-2-ol to afford the title compound, m.p. 270°-274°, (2.5 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 6 hours
  3. filtrationthe solid filtered off
  4. dissolutiondissolved in chloroform
  5. washThe organic phase was washed with water (2×25 cm3)
  6. customdried (MgS04)
  7. customevaporated in vacuo
  8. customto give a solid which
  9. customwas recrystallised from propan-2-ol

Sources & evidence

ORD record
ord-4307b60adff34caaa2fea067176fbf32
Source dataset
uspto-grants-1988_03
Patent number
US04728654

Reaction notes

Loading…