4-Methyloxybenzyl chloride → HCID 67504897, compound

HRID 574289Notes

Reaction equation

HRID 574289 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]=[CH:4][CH:3]=1.[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19]Cl)=[CH:17][CH:16]=1>[N+](CCCC)(CCCC)(CCCC)CCCC.[I-].CN(C=O)C>[Cl:1][C:2]1[C:11]2[C:6](=[C:7]([O:12][CH2:19][C:18]3[CH:21]=[CH:22][C:15]([O:14][CH3:13])=[CH:16][CH:17]=3)[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 699934-Methyloxybenzyl chlorideHCID 3841644-chloroquinolin-8-ol

Product 1

HCID 67504897HCID 67504897, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of compound 22 (3.20 g, 17.82 mmol), p-methoxybenzyl chloride (8.37 g, 53.45 mmol), K2OC3 (7.38 g, 53.45 mmol), and n-Bu4NI (1.65 g, 4.45 mmol) in anhydrous DMF (20 mL) was heated at 80° C. for 10 hours. The reaction mixture was extracted with ethyl acetate (3×100 mL), washed with water, dried over Na2SO4, filtered, and concentrated. The crude material was purified by silica gel column chromatography (Hexane/EtOAc, 3:2) to give 4.75 g (89%) of 23 as yellow solid. 1H NMR (400 MHz, CDCl3) δ ppm 3.81 (s, 3H), 5.38 (s, 2H), 6.78-6.98 (m, 2H), 7.13 (d, 1H, J=7.6 Hz), 7.34-7.60 (m, 4H), 7.80 (d, 1H, J=8.8 Hz), 8.76-8.88 (m, 1H).

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate (3×100 mL)
  2. washwashed with water
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified by silica gel column chromatography (Hexane/EtOAc, 3:2)

Sources & evidence

ORD record
ord-2791a07f1d87452b86ed9ede944d25c1
Source dataset
uspto-grants-2015_05
Patent number
US09034877B2

Reaction notes

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