Potassium Carbonate → HCID 66760295, compound

HRID 889218Notes

Reaction equation

HRID 889218 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[C:7]([OH:12])[CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:13])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH2:2]([O:12][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[N:5]=[C:4]([CH3:13])[CH:3]=[C:2]2[Cl:1])[C:11]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 122197224-Chloro-8-hydroxy-2-methylquinoline

Product 1

HCID 66760295HCID 66760295, compoundYield 77.8%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
70 °C

Procedure

To 4-chloro-2-methylquinolin-8-ol (10.20 g, 52.7 mmol), potassium carbonate (10.9 g, 79.0 mmol) in 2-butanone (100 mL) was added benzyl bromide (6.89 mL, 58.0 mmol) vial syringe with stirring. The suspension was heated at 70° C. for 4 h, stirred at ambient temperature overnight and poured into ice water (200 mL). The precipitate was filtered, washed with a little EtOAc/water and dried to give 8-(benzyloxy)-4-chloro-2-methylquinoline (5.82 g). The filtrate was extracted with EtOAc, dried, filtered and evaporated. Solid from Hex/EtOAc (10/1) was filtered and dried to give additional 8-(benzyloxy)-4-chloro-2-methylquinoline, 13.72 g (92% total crude yield).

Workup

  1. stirringstirred at ambient temperature overnight
  2. filtrationThe precipitate was filtered
  3. washwashed with a little EtOAc/water
  4. customdried

Sources & evidence

ORD record
ord-7fd8fcf9bad24209b37f5e8583b1704e
Source dataset
uspto-grants-2012_08
Patent number
US08252793B2

Reaction notes

Loading…