Diethylethanolamine → Ethyl 2-(2-diethylaminoethoxy)-5-nitrobenzoate

HRID 735102Notes

Reaction equation

F[C:2]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH2:16]([N:18]([CH2:22][CH3:23])[CH2:19][CH2:20][OH:21])[CH3:17].[H-].[Na+]>CN(C=O)C>[CH2:16]([N:18]([CH2:22][CH3:23])[CH2:19][CH2:20][O:21][C:2]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH3:17]

Participants

Conditions

Temperature: 0 °C

Procedure

1.06 g (5.00 mmol) of ethyl 2-fluoro-5-nitrobenzoate and 0.58 mL (5.00 mmol) of 2-diethylaminoethanol are dissolved in 20 mL of DMF and at 0° C. 0.36 g (7.45 mmol) of sodium hydride (50%) is added. The mixture is stirred for 45 minutes at 0° C., poured onto ice water, and finally extracted three times with ethyl acetate. The organic phase is dried over sodium sulfate, the solvent is eliminated and the residue is purified through a silica gel column with petroleum ether/ethyl acetate (4:1) as eluant. Yield: 0.30 g (19% of theory); C15H22N2O5 (M=310.35); calc.: molecular ion peak (M+H)+: 311; found: molecular ion peak (M+H)+: 311; Rf value: 0.1 (silica gel, petroleum ether/ethyl acetate (4:1)).

Workup

additionpoured onto ice water
extractionfinally extracted three times with ethyl acetate
dry with materialThe organic phase is dried over sodium sulfate
customthe residue is purified through a silica gel column with petroleum ether/ethyl acetate (4:1) as eluant

Sources & evidence

ORD record: ord-fbd0a7c03349440b94cc21b8d101be40
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592373B2

Reaction notes

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