Ethanolamine → HC Yellow no. 14

HRID 1111302Notes

Reaction equation

HRID 1111302 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].Cl[C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][C:7]=1[N+:14]([O-:16])=[O:15]>O>[OH:2][CH2:1][CH2:3][NH:4][C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][C:7]=1[N+:14]([O-:16])=[O:15]

Participants

4

Reactant 2

HCID 700EthanolamineHCID 13655Benzonitrile, 4-chloro-3-nitro-

Product 1

HCID 15001944HC Yellow no. 14Yield 96.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Monoethanolamine (38 ml; 0.62 mol) was added to a suspension of 4-chloro-3-nitrobenzonitrile (51.6 g; 0.28 mol) in 270 ml water. The reaction mixture was refluxed for one hour at 100°-110° C. (oil bath). After cooling to room temperature, the orange precipitate was filtered, washed with water and air-dried to give 55.8 g 4-(2-hydroxyethylamino)-3-nitrobenzonitrile (m.p.=132°-134° C.). The yield was about 95%, with the overall yield for the reaction sequence, illustrated below, being about 81%. ##STR6##

Workup

  1. temperatureThe reaction mixture was refluxed for one hour at 100°-110° C. (oil bath)
  2. filtrationthe orange precipitate was filtered
  3. washwashed with water
  4. customair-dried

Sources & evidence

ORD record
ord-8f822e722a3a4fa9ae12fe3f33c8666b
Source dataset
uspto-grants-1990_12
Patent number
US04980158

Reaction notes

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