Glycerol → 6-Bromoquinoline

HRID 1593998Notes

Reaction equation

HRID 1593998 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[N+]([C:12]1[CH:17]=CC=C[CH:13]=1)([O-])=O.OCC(CO)O.B(O)(O)O.OS(O)(=O)=O.[OH-].[Na+]>O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Fe+2]>[Br:1][C:2]1[CH:8]=[C:7]2[C:5](=[CH:4][CH:3]=1)[N:6]=[CH:17][CH:12]=[CH:13]2

Participants

8

Reactant 6

HCID 753GlycerolHCID 1118Sulfuric AcidHCID 7416NitrobenzeneHCID 7628Boric AcidHCID 78074-BromoanilineHCID 14798Sodium Hydroxide

Product 1

HCID 792436-BromoquinolineYield 22.1%

Reagents, catalysts & solvents 1

HCID 62662Ferrous sulfate heptahydrateCatalyst

Procedure

To a mixture of 24 g (140.0 mmol) of 4-bromoaniline, 8.2 ml (80.0 mmol) of nitrobenzene, 38.7 ml (530.0 mmol) of glycerol, 4.7 g (17 mmol) of iron sulfate heptahydrate, and 8.65 g (140 mmol) of boric acid there were added, at −10° C., 22.5 ml of conc. H2SO4. The reaction mixture was then heated under reflux over a period of 10 h. Following adjustment of the pH to pH>12 with a 50% strength aq. NaOH solution there were obtained from the residue 3.69 g (17.7 mmol, 13%) of 6-bromoquinoline by steam distillation.

Workup

  1. additionthere were added, at −10° C.
  2. temperatureThe reaction mixture was then heated
  3. temperatureunder reflux over a period of 10 h

Sources & evidence

ORD record
ord-30f8ed56189e4d078bf58639e5e8d5a3
Source dataset
uspto-grants-2007_11
Patent number
US07300939B2

Reaction notes

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