Carbon Dioxide → 8-Bromo-5-methoxyquinolin-4-ol

HRID 1437360Notes

Reaction equation

HRID 1437360 reaction equation
C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1.[Br:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][C:28]=1[NH:35][CH:36]=[C:37]1[C:42](=[O:43])OC(C)(C)OC1=O.C(=O)=O>CC(C)=O>[Br:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[C:29]2[C:28]=1[NH:35][CH:36]=[CH:37][C:42]2=[O:43]

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)HCID 686990625-[(2-Bromo-5-methoxy-phenylamino)-methylene]-2,2-dimethyl-[1,3]dioxane-4,6-dione

Product 1

HCID 497579588-Bromo-5-methoxyquinolin-4-olYield 76%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Dowtherm A (30 ml) was heated to reflux and enamine (a) (10 g) was added portionwise (CAUTION—vigorous evolution of CO2 and acetone) over 2 minutes. Heating was continued for a further 2 minutes then the mixture was allowed to cool to room temperature. Filtration and drying in vacuo afforded a brown solid (5.4 g, 76%).

Workup

  1. temperatureto reflux
  2. temperatureHeating
  3. filtrationFiltration
  4. customdrying in vacuo

Sources & evidence

ORD record
ord-3df9479c37364ed497bb199194cd34dd
Source dataset
uspto-grants-2009_11
Patent number
US07622481B2

Reaction notes

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