Benzyl Bromide → HCID 178515619, compound

HRID 1777171Notes

Reaction equation

HRID 1777171 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].[CH:13]1[CH:18]=[CH:17][C:16]([CH2:19]Br)=[CH:15][CH:14]=1.C1CCN2C(=NCCC2)CC1>CC(O)C>[CH2:19]([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:16]1[CH:17]=[CH:18][CH:13]=[CH:14][CH:15]=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 85%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of quinoline-2,8-diol (5.0 g, 31.1 mmol) in i-PrOH (50 mL) was added BnBr (5.31 g, 31.1 mmol) and DBU (2.02 g, 5.32 mmol). The mixture was stirred at 80° C. for 16 h. The mixture was evaporated and to the residue was added DCM (100 mL), and this solution was washed with 0.5 N NaOH (50 mL), 10% HCl (50 mL), and H2O (50 mL). The organic layer was evaporated to give the desired compound (6.6 g, yield 85%). 1HNMR (CDCl3, 400 MHz) δ: 9.16 (br. s., 1H), 7.74 (d, J=9.8 Hz, 1H), 7.49-7.36 (m, 5H), 7.20-7.10 (m, 2H), 7.09-7.03 (m, 1H), 6.67 (d, J=9.5 Hz, 1H), 5.19 (s, 2H).

Workup

  1. customThe mixture was evaporated and to the residue
  2. additionwas added DCM (100 mL)
  3. washthis solution was washed with 0.5 N NaOH (50 mL), 10% HCl (50 mL), and H2O (50 mL)
  4. customThe organic layer was evaporated

Sources & evidence

ORD record
ord-29ba0d1bfc004577a00d264e22b484fc
Source dataset
uspto-grants-2016_02
Patent number
US09266836B2

Reaction notes

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