Ethanolamine → 2-(beta-Hydroxyethyl)amino-6-(beta-hydroxyethyl)aminonitrobenzene

HRID 981814Notes

Reaction equation

HRID 981814 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4](Cl)[C:3]=1[N+:9]([O-:11])=[O:10].[CH2:12]([CH2:14][NH2:15])[OH:13]>>[OH:13][CH2:12][CH2:14][NH:15][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH:15][CH2:14][CH2:12][OH:13])[C:3]=1[N+:9]([O-:11])=[O:10]

Participants

3

Reactant 2

HCID 700EthanolamineHCID 117591,3-Dichloro-2-nitrobenzene

Product 1

HCID 197511312-(beta-Hydroxyethyl)amino-6-(beta-hydroxyethyl)aminonitrobenzene

Conditions

Temperature
98 °C

Procedure

0.25 mole (48 g) of 2,6-dichloronitrobenzene, prepared according to the method described by Alexander McKillop and Jonathan A. Tarbin in Tetrahedron Letters, Vol. 24 No. 14, page 1505 (1983), is added to 200 ml of ethanolamine. The mixture is heated to 98° C. for 8 hours. The reaction mixture is poured onto ice. After phase separation, the precipitate is taken up in the minimum quantity of ethanol, with stirring. After dilution with a mixture of ice and water, the expected product is filtered off, washed with water and then recrystallized from ethanol. It is identical with the product prepared in Example 1.

Workup

  1. additionThe reaction mixture is poured onto ice
  2. customAfter phase separation
  3. additionAfter dilution with a mixture of ice and water
  4. filtrationthe expected product is filtered off
  5. washwashed with water
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-63c482566b8249aa8fb33439c98ffa19
Source dataset
uspto-grants-1991_02
Patent number
US04992586

Reaction notes

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