Benzyl Chloride → HCID 67057987, compound

HRID 2188605Notes

Reaction equation

HRID 2188605 reaction equation
[CH3:1][O:2][C:3]1[C:12]([OH:13])=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1.C([O-])([O-])=O.[K+].[K+].[CH2:20](Cl)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(#N)C.C(Cl)Cl>[CH3:1][O:2][C:3]1[C:12]([O:13][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 128498147-Methoxyquinolin-8-ol

Product 1

HCID 67057987HCID 67057987, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

7-Methyloxy-8-hydroxyquinoline (1.10 g; 6.29 mmol) and K2CO3 (1.30 g; 9.43 mmol) in 30 ml of dry acetonitrile are stirred for 10 minutes under argon. Benzyl chloride (0.87 ml, 7.54 mmol) is then added and the reaction medium is heated under reflux overnight. After returning to ambient temperature, the precipitate is filtered, washed with CH2Cl2 and the filtrate is concentrated under reduced pressure. The oil obtained is dissolved again in CH2Cl2 (50 ml) and washed in succession with an aqueous solution of NaOH 2 N (4×50 ml) and water (1×50 ml). The organic phase is dried over anhydrous Na2SO4 and the solvent is evaporated under reduced pressure to yield 7-methyloxy-8-[(phenylmethyl)oxy]quinoline in the form of a brown oil (1.28 g; 4.84 mmol, yield=77%). NMR-1H (250 MHz, CDCl3) δ, ppm: 8.94 (dd, 3J (H, H)=4.0 Hz, 4J (H, H)=1.5 Hz, 1H); 8.06 (dd, 3J (H, H)=8.5 Hz, 4J (H, H)=1.5 Hz, 1H); 7.59-7.51 (m, 3H); 7.36-7.24 (m, 5H); 5.40 (s, 2H); 3.92 (s, 3H). NMR-13C (63 MHz, CDCl3) δ, ppm: 151.3 (CH); 149.5 (Cq); 142.9 (Cq); 141.2 (Cq); 137.4 (Cq); 135.3 (CH); 127.9 (CH); 127.4 (CH); 127.1 (CH); 123.6 (Cq); 122.9 (CH); 118.5 (CH) 114.8 (CH); 75.2 (CH2); 56.1 (CH3). MS (CID, NH3): m/z=266 (MH+). Analysis (%) for C17H15NO2.0.05 CHCl3: calculated C, 75.49; H, 5.59; N, 5.16. found C, 75.74; H, 5.40; N, 5.33.

Workup

  1. temperaturethe reaction medium is heated
  2. temperatureunder reflux overnight
  3. customAfter returning to ambient temperature
  4. filtrationthe precipitate is filtered
  5. washwashed with CH2Cl2
  6. concentrationthe filtrate is concentrated under reduced pressure
  7. customThe oil obtained
  8. washwashed in succession with an aqueous solution of NaOH 2 N (4×50 ml) and water (1×50 ml)
  9. dry with materialThe organic phase is dried over anhydrous Na2SO4
  10. customthe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-2c170c51c2d546bda416ed74d5177c9b
Source dataset
uspto-grants-2012_12
Patent number
US08324196B2

Reaction notes

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