N-methyl-2-pyrrolidone → HCID 57841525, compound

HRID 734157Notes

Reaction equation

HRID 734157 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[CH3:11].CN1CCCC1=O.[OH:19][CH2:20][CH2:21][N:22]([CH2:26][CH2:27][OH:28])[CH2:23][CH2:24][NH2:25]>C(N(CC)CC)C>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([NH:25][CH2:24][CH2:23][N:22]([CH2:26][CH2:27][OH:28])[CH2:21][CH2:20][OH:19])=[C:3]([CH3:11])[CH:4]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 68001Benzene, 1-fluoro-2-methyl-4-nitro-HCID 98535N,N-Bis(2-hydroxyethyl)ethylenediamine

Product 1

HCID 57841525HCID 57841525, compoundYield 41.1%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
80 °C

Procedure

2 g of 2-fluoro-5-nitrotoluene were added to a solution of 30 ml of N-methylpyrrolidinone, 2.29 g of N,N-bis(2-hydroxyethyl)ethylenediamine, and 1.72 g of triethylamine. The reaction medium was heated at 80° C. for 10 hours and, after cooling to room temperature, was poured into a water/ice mixture. The resulting medium was extracted with ethyl acetate and the organic phase was then concentrated under vacuum. 1.5 g of 2[[2-(4-nitro-2-methylphenylamino)ethyl]-(2-hydroxyethyl)amino]ethanol (17) were obtained.

Workup

  1. temperatureafter cooling to room temperature
  2. extractionThe resulting medium was extracted with ethyl acetate
  3. concentrationthe organic phase was then concentrated under vacuum

Sources & evidence

ORD record
ord-b8d5f460ab77467e8b9e51a52fd4f7a7
Source dataset
uspto-grants-2009_09
Patent number
US07591860B2

Reaction notes

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