Ethanolamine → N-(2-Hydroxyethyl)-3-nitrobenzeneacetamide

HRID 1060227Notes

Reaction equation

HRID 1060227 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][C:11]([OH:13])=O)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[CH2:14]([CH2:16][NH2:17])[OH:15].C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1>CN(C=O)C>[OH:15][CH2:14][CH2:16][NH:17][C:11](=[O:13])[CH2:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1

Participants

6

Reactant 4

HCID 700EthanolamineHCID 8471TriethylamineHCID 158763-Nitrophenylacetic acidHCID 2724699PyBOP

Product 1

HCID 22475311N-(2-Hydroxyethyl)-3-nitrobenzeneacetamideYield 26%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 3-nitrophenylacetic acid (3.21 g, 17.7 mmol), ethanolamine (2.8 g, 46 mmol), and triethylamine (3.0 mL, 22 mmol) in anhydrous DMF (110 mL) was added a solution of benzotriazole-1-yl-oxy-tris-pyrrolidino-phosphonium hexafluorophosphate (PyBOP, 9.37 g, 18.0 mmol) in anhydrous DMF (80 mL). After stirring 16 hours at ambient temperature (under nitrogen), the reaction mixture was concentrated in vacuo, dissolved in DCM and filtered. The filtrate was washed with 10% aqueous citric acid, saturated aqueous NaHCO3, pH 7 buffer, and brine, dried over Na2SO4 and filtered. The evaporated filtrate was then purified by flash chromatography (10% methanol in DCM) giving the title compound (1.02 g, 26%) as a light yellow solid. 1H NMR (300 MHz, CDCl3/CD3OD) δ 8.18 (m, 1H), 8.11 (ddd, 1H, J=8.1 Hz, 2.4 Hz, 1.1 Hz), 7.72 (m, 1H), 7.60 (t, 1H, J=7.8 Hz), 3.62 (s, 2H), 3.44 (t, 2H, J=5.9 Hz), 3.16 (t, 2H, J=5.9 Hz).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. dissolutiondissolved in DCM
  3. filtrationfiltered
  4. washThe filtrate was washed with 10% aqueous citric acid, saturated aqueous NaHCO3, pH 7 buffer
  5. dry with materialbrine, dried over Na2SO4
  6. filtrationfiltered
  7. customThe evaporated filtrate was then purified by flash chromatography (10% methanol in DCM)

Sources & evidence

ORD record
ord-8c964717aa6c4a24ac36e6069997aa77
Source dataset
uspto-grants-2003_02
Patent number
US06521663B2

Reaction notes

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