Reaction #355734

ord-380b56030e494935b169924ff1029747

Reaction equation

Cc1cc([N+](=O)[O-])ccc1F
4-fluoro-3-methyl nitrobenzene
NCCNCCO
2-(2-aminoethylamino)ethanol
O=C([O-])[O-].[K+].[K+]
K2CO3
CN1CCCC1=O
N-methylpyrrolidinone
Cc1cc([N+](=O)[O-])ccc1NCCNCCO
2-[2-(4-nitro-2-methylphenylamino)ethylamino]ethanol
Yield 77.8%

Solvents

Conditions

Temperature
60°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Temperatureafter cooling to room temperature
  2. 2
    OtherThe yellow precipitate formed
  3. 3
    Filtrationwas filtered off
  4. 4
    Dryingdried over P2O5

Procedure

2 g of 4-fluoro-3-methyl nitrobenzene, 1.61 g of 2-(2-aminoethylamino)ethanol and 2.14 g of K2CO3 were added to a solution of 20 ml of N-methylpyrrolidinone. The reaction medium was heated at 60° C. for 7 hours and, after cooling to room temperature, was then poured into a water and ice mixture. The yellow precipitate formed was filtered off, reslurried in water and then dried over P2O5. 2.4 g of 2-[2-(4-nitro-2-methylphenylamino)ethylamino]ethanol (5) were obtained.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07445645B2uspto-grants-2008_11