Ethanolamine → 2-[(4-nitrophenyl)amino]ethanol

HRID 2290031Notes

Reaction equation

HRID 2290031 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[CH2:11]([CH2:13][NH2:14])[OH:12]>C(O)C>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([NH:14][CH2:13][CH2:11][OH:12])=[CH:3][CH:4]=1)([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 700EthanolamineHCID 9590p-Fluoronitrobenzene

Product 1

HCID 2661542-[(4-nitrophenyl)amino]ethanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To a pressure tube containing 1-fluoro-4-nitrobenzene (10.6 mL) and absolute ethanol (20 mL) under an atmosphere of argon gas is added ethanolamine (7.2 mL). The reaction is tightly capped and heated to 90° C. After 1 hour, the reaction is cooled to room temperature and concentrated under reduced pressure. The residue is dried in vacuo. The solid is crystallized from 95% ethanol to give 4.1 g of 2-(4-nitroanilino)-1-ethanol as yellow crystals.

Workup

  1. customThe reaction is tightly capped
  2. temperaturethe reaction is cooled to room temperature
  3. concentrationconcentrated under reduced pressure
  4. customThe residue is dried in vacuo
  5. customThe solid is crystallized from 95% ethanol

Sources & evidence

ORD record
ord-97e134f790f74027ac787ba1469d9c3e
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

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