Malonic Acid → HCID 178524624, compound

HRID 2170907Notes

Reaction equation

HRID 2170907 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=O.C(O)(=O)[CH2:14][C:15]([OH:17])=[O:16]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]=[C:6]([OH:11])[CH:5]=[C:14]2[C:15]([OH:17])=[O:16]

Participants

4

Reactant 2

HCID 867Malonic AcidHCID 68895-Bromoisatin

Product 1

HCID 178524624HCID 178524624, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-bromoindoline-2,3-dione (0.250 g) was dissolved in THF (3 ml) in a round-bottomed flask and malonic acid (2 eq) was added. The vessel was connected to a reflux condenser and heated to reflux overnight by conventional heating. After 12 hours, solid precipitate was observed. Suspension was concentrated under reduced pressure to remove solvent, water was added, and the suspension was refluxed for 4 hours. The suspension was then filtered to provide 6-bromo-2-hydroxyquinoline-4-carboxylic acid (0.150 g) as a solid.

Workup

  1. customThe vessel was connected to a reflux condenser
  2. temperatureheated
  3. temperatureto reflux overnight by conventional heating
  4. concentrationSuspension was concentrated under reduced pressure
  5. customto remove solvent, water
  6. additionwas added
  7. temperaturethe suspension was refluxed for 4 hours
  8. filtrationThe suspension was then filtered

Sources & evidence

ORD record
ord-3857ff9947c04fb18bffc7dafbc37d9a
Source dataset
uspto-grants-2015_06
Patent number
US09051305B2

Reaction notes

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