Ethanolamine → HC Yellow no. 12

HRID 1494353Notes

Reaction equation

HRID 1494353 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH2:12]([CH2:14][NH2:15])[OH:13]>C(O)CCC>[OH:13][CH2:12][CH2:14][NH:15][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

Participants

4

Reactant 2

HCID 700EthanolamineHCID 69772,5-Dichloronitrobenzene

Product 1

HCID 5182864HC Yellow no. 12Yield 75%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

To a solution of 10 g (52 mmol) 2,5-dichloronitrobenzene in 40 ml butanol was added 6.5 g (104 mmol) ethanolamine, and the mixture was refluxed for 20 h. The reaction mixture was evaporated in vacuo. The residue was recrystallized (toluene) to give 8.1 g (75%) N-(2-hydroxyethyl)-4-chloro-2-nitroaniline. M.p. 98°-100° C.

Workup

  1. temperaturethe mixture was refluxed for 20 h
  2. customThe reaction mixture was evaporated in vacuo
  3. customThe residue was recrystallized (toluene)

Sources & evidence

ORD record
ord-1a2fd3ed3b8c44cabddfd871c438b13f
Source dataset
uspto-grants-1991_06
Patent number
US05026704

Reaction notes

Loading…