Benzyl Bromide → HCID 178515619, compound

HRID 1437327Notes

Reaction equation

HRID 1437327 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[OH:11])[CH:4]=[CH:3][C:2]=1[OH:12].N12CCCN=C1CCCCC2.[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(O)(C)C>[CH2:24]([O:11][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[N:1]=[C:2]([OH:12])[CH:3]=[CH:4]2)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 178515617HCID 178515617, compound

Product 1

HCID 178515619HCID 178515619, compoundYield 77.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

This was prepared by a slight modification of the procedure of Guo et al, Tet Lett, 1999, 40, 6999. To a stirred solution of 2,8-quinolinediol (4.97 g, 30.84 mmol) and 1,8-diazabicylo[5.4.0]undec-7-ene (DBU) (40.2 mmol, 6 mL) in isopropyl alcohol (60 mL) was added benzyl bromide (3.7 mL, 30.84 mmol). The solution was heated at reflux overnight. The reaction mixture was allowed to cool and then concentrated in vacuo. The resulting residue was diluted with CH2Cl2 and washed with 0.5 N NaOH, 10% HCl and water and dried over Na2SO4. Concentration provided 6 g (77%) of a tan solid, which was used without further purification.

Workup

  1. customThis was prepared by a slight modification of the procedure of Guo et al, Tet Lett, 1999, 40, 6999
  2. temperatureThe solution was heated
  3. temperatureat reflux overnight
  4. temperatureto cool
  5. concentrationconcentrated in vacuo
  6. additionThe resulting residue was diluted with CH2Cl2
  7. washwashed with 0.5 N NaOH, 10% HCl and water
  8. dry with materialdried over Na2SO4
  9. concentrationConcentration

Sources & evidence

ORD record
ord-480d34707179449ba31d68dab17e0634
Source dataset
uspto-grants-2009_11
Patent number
US07622481B2

Reaction notes

Loading…