2',4'-Dihydroxyacetophenone → 1-[2-Hydroxy-4-(quinolin-2-ylmethoxy)-phenyl]-ethanone

HRID 892182Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10].Cl.ClCC1C=C(C=CC=1)O[CH2:19][C:20]1[CH:29]=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:21]=1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[OH:1][C:2]1[CH:7]=[C:6]([O:8][CH2:19][C:20]2[CH:29]=[CH:28][C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[N:21]=2)[CH:5]=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10]

Participants

Conditions

Temperature: 50 °C

Procedure

2′,4′-Dihydroxy-acetophenone (912 mg, 6 mmol) and 2-chloromethyl-quinoline hydrochloride (856 mg, 4.0 mmol, example 49) are dissolved in acetonitrile (20 mL). K2CO3 (1.12 g, 8.0 mmol) is added and the contents are heated to 50° C. for 16 hrs. The reaction is cooled to room temperature, and the solvent is removed by rotary evaporation. The contents are partitioned between ethyl acetate (100 mL) and water (100 mL), the aqueous layer is acidified with 2 N HCl to ˜pH 2 and further extracted with ethyl acetate (2×50 mL). All organic fractions are combined and washed with brine (3×150 mL), dried over MgSO4 and concentrated. The crude material is preadsorbed onto silica gel and purified by flash chromatography (silica, 15% ethyl acetate in hexanes) to give the title compound; MS (ion spray) 294 (M+H)+.

Workup

temperatureThe reaction is cooled to room temperature
customthe solvent is removed by rotary evaporation
customThe contents are partitioned between ethyl acetate (100 mL) and water (100 mL)
extractionfurther extracted with ethyl acetate (2×50 mL)
washwashed with brine (3×150 mL)
dry with materialdried over MgSO4
concentrationconcentrated
custompurified by flash chromatography (silica, 15% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-fb753a3f8b6045faab7fbc956983875d
Source dataset: uspto-grants-2006_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07005440B1

Reaction notes

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