Water → HCID 86629137, compound

HRID 1949061Notes

Reaction equation

HRID 1949061 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([OH:12])[CH:8]=2)[N:3]=1.[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH2:18]Br.C(=O)([O-])[O-].[K+].[K+].O>CC(C)=O>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH2:18][C:17]3[CH:20]=[CH:21][CH:22]=[C:15]([O:14][CH3:13])[CH:16]=3)[CH:8]=2)[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 40672073-Methoxybenzyl bromideHCID 221325772-Chloroquinolin-6-ol

Product 1

HCID 86629137HCID 86629137, compoundYield 44.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-Chloro-6-hydroxy-quinoline (CAS RN 577967-89-6, 0.6 g, 3 mMol) and 3-methoxybenzylbromid (0.56 mL, 0.004 Mol) were dissolved in a slurry of potassium carbonate (0.55 g, 4 mMol) in 15 mL acetone and heated to reflux for 3 hr. Then water was added and the mixture extracted with ethyl acetate (3×20 mL). The combined organic phases were dried on sodium sulfate, filtered and evaporated. The residue was subjected to column chromatography on silica gel (heptane/ethyl acetate 10:0→9:1→4:1 gradient) to yield 2-chloro-6-(3-methoxy-benzyloxy)-quinoline (0.40 g, 40%) as a colorless solid; MS: m/e=300.3 (M+H+).

Workup

  1. temperatureheated
  2. temperatureto reflux for 3 hr
  3. extractionthe mixture extracted with ethyl acetate (3×20 mL)
  4. customThe combined organic phases were dried on sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-e85a8ddb74ce45468876bb337f1da510
Source dataset
uspto-grants-2013_03
Patent number
US08399674B2

Reaction notes

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