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

HRID 2184209Notes

Reaction equation

HRID 2184209 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-8378afa3873049d0844d5d4aa45f799a
Source dataset
uspto-grants-2005_05
Patent number
US06900231B2

Reaction notes

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