1,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene) → Methyl 8-bromo-4-oxo-1,4-dihydroquinoline-6-carboxylate

HRID 1778263Notes

Reaction equation

HRID 1778263 reaction equation
C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1.[Br:26][C:27]1[CH:28]=[C:29]([CH:34]=[CH:35][C:36]=1[NH:37][CH:38]=[C:39]1[C:44](=[O:45])OC(C)(C)OC1=O)[C:30]([O:32][CH3:33])=[O:31]>>[Br:26][C:27]1[CH:28]=[C:29]([C:30]([O:32][CH3:33])=[O:31])[CH:34]=[C:35]2[C:36]=1[NH:37][CH:38]=[CH:39][C:44]2=[O:45]

Participants

3

Reactant 2

HCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)HCID 118323992Methyl 3-bromo-4-(((2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl)amino)benzoate

Product 1

HCID 118324114Methyl 8-bromo-4-oxo-1,4-dihydroquinoline-6-carboxylate

Procedure

To a flask with DOWTHERM (35 mL) at 210° C. was added methyl 3-bromo-4-(((2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl)amino)benzoate (3.3 g, 8.59 mmol) in portions. The resulting solution was heated for 20 min and cooled down to room temperature. Solids were precipitated from the solution. To the reaction mixture was then added hexanes and the precipitate filtered. The solids were washed thoroughly with Et2O and hexanes and dried under vacuum to yield methyl 8-bromo-4-oxo-1,4-dihydroquinoline-6-carboxylate. (M+H)+: 282, 284

Workup

  1. temperatureThe resulting solution was heated for 20 min
  2. customSolids were precipitated from the solution
  3. filtrationadded hexanes and the precipitate filtered
  4. washThe solids were washed thoroughly with Et2O and hexanes
  5. customdried under vacuum

Sources & evidence

ORD record
ord-28498b60af3b45e889b0270398358159
Source dataset
uspto-grants-2016_02
Patent number
US09266835B2

Reaction notes

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