Cesium carbonate → 2-(2-Dimethylamino-ethoxy)-4-methoxy-benzonitrile

HRID 1167312Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 2-hydroxy-4-methoxy-benzonitrile (200 mg, 1.341 mmol) in acetone (5 mL) were added cesium carbonate (1.312 g, 4.023 mmol) and (2-chloroethyl)-dimethylamine hydrochloride (390 mg, 2.682 mmol). The resulting mixture was heated at 60° C. for overnight. The solid was filtered off and washed with methylene chloride (6×10 mL). The filtrate was washed with sodium bicarbonate solution, brine and dried over anhydrous sodium sulfate. The solid was then filtered off, and the filtrate was concentrated in vacuo. Purification of the residue by flash chromatography (Biotage system, KP-Sil™ 32-63 μm, 60 Å silica gel) eluting with 0-5% methanol in methylene chloride yielded 2-(2-dimethylamino-ethoxy)-4-methoxy-benzonitrile as a pale-yellow oil (210 mg, 71%).

Workup

filtrationThe solid was filtered off
washwashed with methylene chloride (6×10 mL)
washThe filtrate was washed with sodium bicarbonate solution, brine
dry with materialdried over anhydrous sodium sulfate
filtrationThe solid was then filtered off
concentrationthe filtrate was concentrated in vacuo
customPurification of the residue by flash chromatography (Biotage system, KP-Sil™ 32-63 μm, 60 Å silica gel)
washeluting with 0-5% methanol in methylene chloride

Sources & evidence

ORD record: ord-a0b20c241e9e44b195fee19f537b13a1
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06617346B1

Reaction notes

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