N-methyl-2-pyrrolidone → HCID 23104601, compound

HRID 734149Notes

Reaction equation

HRID 734149 reaction equation
F[C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH3:8])[CH:7]=1.CN1CCCC1=O.[NH2:19][CH2:20][CH:21]([OH:24])[CH2:22][OH:23]>C(N(CC)CC)C>[N+:9]([C:5]1[CH:4]=[CH:3][C:2]([NH:19][CH2:20][CH:21]([OH:24])[CH2:22][OH:23])=[CH:7][C:6]=1[CH3:8])([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 735613-Amino-1,2-propanediolHCID 949565-Fluoro-2-nitrotoluene

Product 1

HCID 23104601HCID 23104601, compoundYield 9.6%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
60 °C

Procedure

2 g of 5-fluoro-2-nitrotoluene were added to a solution of 20 ml of N-methylpyrrolidinone, 1.41 g of 3-amino-1,2-propanediol, and 1.57 g of triethylamine. The reaction medium was heated at 60° 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. 0.28 g of 3-(4-nitro-3-methylphenylamino)propane-1,2-diol (9) was 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-57e0eac011eb4325bbfd2a130555809e
Source dataset
uspto-grants-2009_09
Patent number
US07591860B2

Reaction notes

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