Water → HCID 67056944, compound

HRID 517520Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:9][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=[C:12]([CH3:20])[CH:11]=1.[OH:21][C:22]1[CH:37]=[CH:36][C:25]([C:26]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:27])=[CH:24][CH:23]=1.O>CN(C)C=O>[CH3:20][C:12]1[CH:11]=[C:10]([CH2:9][O:21][C:22]2[CH:37]=[CH:36][C:25]([C:26]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[O:27])=[CH:24][CH:23]=2)[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=1

Participants

Conditions

Temperature: 60 °C

Procedure

3.6 g (26.3 mmol) of potassium carbonate, 5 g (21.9 mmol) of 4-chloromethyl-2-methylquinoline hydrochloride and 5.2 g (23 mmol) of benzyl 4-hydroxybenzoate are put into solution in 30 ml of dimethylformamide. The reaction medium is heated at 60° C. for 18 h then water is added. After extracting with ethyl acetate, the organic phase is washed with water then with a saturated aqueous solution of sodium chloride, dried over magnesium sulphate, filtered and concentrated under vacuum. The crude product is purified by chromatography over silica gel eluted with a 70/30 heptane/ethyl acetate mixture. 3.6 g (43%) of benzyl 4-(2-methylquinolin-4-ylmethoxy)benzoate are obtained in the form of a light-yellow solid.

Workup

extractionAfter extracting with ethyl acetate
washthe organic phase is washed with water
dry with materialwith a saturated aqueous solution of sodium chloride, dried over magnesium sulphate
filtrationfiltered
concentrationconcentrated under vacuum
customThe crude product is purified by chromatography over silica gel
washeluted with a 70/30 heptane/ethyl acetate mixture

Sources & evidence

ORD record: ord-763d48222841401b88b197eda6650067
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115102B2

Reaction notes

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