Toluene → HCID 178498494, compound

HRID 545217Notes

Reaction equation

HRID 545217 reaction equation
[C:1]([C:7]([O:9][CH3:10])=[O:8])#[C:2][C:3](OC)=[O:4].[Br:11][C:12]1[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=1[NH2:14].O(C1C=CC=CC=1)C1C=CC=CC=1.C1(C)C=CC=CC=1>CO.CCCCCC>[Br:11][C:12]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:13]=1[N:14]=[C:1]([C:7]([O:9][CH3:10])=[O:8])[CH:2]=[C:3]2[OH:4]

Participants

7

Reactant 4

HCID 1140TolueneHCID 7583Diphenyl EtherHCID 119922-BromoanilineHCID 12980Dimethyl acetylenedicarboxylate

Product 1

HCID 178498494HCID 178498494, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8058HexaneSolvent

Procedure

27 ml of dimethyl acetylenedicarboxylate was added to a solution of 34.4 g of 2-bromoaniline in 200 ml of MeOH placed in a 1 L-flask at room temperature. The mixture was stirred overnight at room temperature. The mixture was concentrated in vacuo to afford a yellow oil. The crude product was added to 200 ml of Ph2O placed in 1 L-flask heated at 250° C. The mixture was stirred for 15 min at the same temperature and then cooled to room temperature. 200 ml of toluene and 200 ml of hexane was added to the mixture. The slurry was stirred for 1 h with cooling at 0 deg C. The resulting solid was filtered, washed with hexane, and dried under vacuum to afford methyl 8-bromo-4-hydroxyquinoline-2-carboxylate as an off-white solid.

Workup

  1. customplaced in a 1 L-flask at room temperature
  2. concentrationThe mixture was concentrated in vacuo
  3. customto afford a yellow oil
  4. temperatureheated at 250° C
  5. stirringThe mixture was stirred for 15 min at the same temperature
  6. temperaturecooled to room temperature
  7. stirringThe slurry was stirred for 1 h
  8. temperaturewith cooling at 0 deg C
  9. filtrationThe resulting solid was filtered
  10. washwashed with hexane
  11. customdried under vacuum

Sources & evidence

ORD record
ord-ab7e1825e2674d7eabcadf1ca9c6d19e
Source dataset
uspto-grants-2011_05
Patent number
US07935712B2

Reaction notes

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