Ethanolamine → Methyl 2-[(2-hydroxyethyl)amino]-3-nitrobenzoate

HRID 1698537Notes

Reaction equation

HRID 1698537 reaction equation
Cl[C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH2:15]([NH2:18])[CH2:16][OH:17]>C1COCC1>[OH:17][CH2:16][CH2:15][NH:18][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 2

HCID 700EthanolamineHCID 10751184Methyl 2-chloro-3-nitrobenzoate

Product 1

HCID 11253443Methyl 2-[(2-hydroxyethyl)amino]-3-nitrobenzoateYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4.70 g (21.9 mmol) of methyl 2-chloro-3-nitrobenzoate in 300 mL of THF was added dropwise 300 mL of 2-ethanolamine (80 mmol) and the mixture was refluxed over night. The reaction was concentrated to dryness, dissolved in ethyl acetate, and washed aqueous sodium hydrogen carbonate and water. The organics were dried over magnesium sulfate, filtered, and concentrated in vacuo to give 5.00 g (20.8 mmol, 95%) of the title compound.

Workup

  1. temperaturethe mixture was refluxed over night
  2. concentrationThe reaction was concentrated to dryness
  3. dissolutiondissolved in ethyl acetate
  4. washwashed aqueous sodium hydrogen carbonate and water
  5. dry with materialThe organics were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2f13086cd1804c98ba47649a0c989326
Source dataset
uspto-grants-2012_04
Patent number
US08163935B2

Reaction notes

Loading…