Ethanolamine → 2-[2-(4-Nitro-phenyl)-ethylamino]-ethanol

Reaction equation

Br[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=1.[NH2:13][CH2:14][CH2:15][OH:16]>>[N+:10]([C:7]1[CH:8]=[CH:9][C:4]([CH2:3][CH2:2][NH:13][CH2:14][CH2:15][OH:16])=[CH:5][CH:6]=1)([O-:12])=[O:11]

Participants

Reactant 2

HCID 700Ethanolamine

HCID 792664-Nitrophenethyl bromide

Product 1

HCID 227227442-[2-(4-Nitro-phenyl)-ethylamino]-ethanol

Conditions

Temperature: 150 °C

Procedure

A mixture of 1-(2-bromo-ethyl)-4-nitro-benzene (86.9 mmoles) and 2-amino-ethanol (869 mmoles) is heated at 150° C. under microwave activation for 10 minutes. The reaction mixture is evaporated to dryness and the residue obtained is purified on silica gel (SiO2; gradient DCM/MeOH) to yield the title product, which is used directly in the next Step.

Workup

customThe reaction mixture is evaporated to dryness
customthe residue obtained
customis purified on silica gel (SiO2; gradient DCM/MeOH)

Sources & evidence

ORD record: ord-2b4fbf189855456f819977f42058ce7e
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541412B2

Reaction notes

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