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

HRID 1466008Notes

Reaction equation

HRID 1466008 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].C(N(CC)CC)C>CN(C=O)C>[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

5

Reactant 3

HCID 700EthanolamineHCID 8471TriethylamineHCID 792664-Nitrophenethyl bromide

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-(2-Bromoethyl)-4-nitrobenzene (5.0 g, 22 mmol), 2-aminoethanol (1.7 g, 28 mmol), and triethylamine (6.6 mL, 48 mmol) was heated to 60° C. for 16 hours in DMF. LC showed formation of the desired product. DMF was removed under reduced pressure, and the residue was dissolved in EtOAc. The desired product was precipitated out with hexanes. LC-MS (IE, m/z): 211 [M+1]+.

Sources & evidence

ORD record
ord-47196034b6654a96a9bb306b68c249df
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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