Water → HCID 86634195, compound

HRID 1671560Notes

Reaction equation

[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[OH:12])[N:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH:20]([O:23][CH:24](CC)Br)[CH2:21]C.O>CC(C)=O.CCCCCCC.C(OCC)(=O)C>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[O:12][CH2:21][CH2:20][O:23][CH3:24])[N:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

2-Chloro-5-hydroxy-quinoline (0.30 g, 1.67 mmol) was dissolved in aceton (10 mL). Potassium carbonate (370 mg, 2.7 mmol) and bromo-ethyl-methylether (250 □L, 2.7 mmol) were added. The reaction mixture was stirred for 18 h at 50° C. After addition of water the reaction mixture was extracted with ethyl acetate (3×50 mL) and the combined organic phases were dried on sodium sulfate. After evaporation of the solvent a brown oil was obtained which was subjected to column chromatography (silica gel, heptane:ethyl acetate 9:1, 4:1) to yield 2-chloro-5-(2-methoxy-ethoxy)-quinoline as a colorless oil (120 mg, 30%); MS: m/e=238.8 (M+H+).

Workup

extractionwas extracted with ethyl acetate (3×50 mL)
customthe combined organic phases were dried on sodium sulfate
customAfter evaporation of the solvent a brown oil
customwas obtained which

Sources & evidence

ORD record: ord-34a3c4d7b5f34a3e9db6df60efea5750
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07994324B2

Reaction notes

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