Ethanolamine → HC Yellow no. 14

HRID 412551Notes

Reaction equation

HRID 412551 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[CH2:13]([CH2:15][NH2:16])[OH:14]>C(O)C.O1CCCC1>[OH:14][CH2:13][CH2:15][NH:16][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11]

Participants

5

Reactant 2

HCID 700Ethanolamine3×HCID 13655Benzonitrile, 4-chloro-3-nitro-

Product 1

HCID 15001944HC Yellow no. 14

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-chloro-3-nitrobenzonitrile (10.13 g) and ethanolamine (3.52 ml) in a mixture of ethanol (150 ml) and tetrahydrofuran (50 ml) was stirred at room temperature for 2 hours. Ethanolamine (3.35 ml) was added and the mixture was stirred at 50° C. for 1 hour. Then, ethanolamine (3.35 ml) was added, and the mixture was stirred at the same temperature for 1 hour. After completion of the reaction, the solvent was evaporated and the obtained solid was washed with isopropanoyl, collected by filtration, and dried under reduced pressure to give the title compound (7.25 g).

Workup

  1. stirringthe mixture was stirred at 50° C. for 1 hour
  2. stirringthe mixture was stirred at the same temperature for 1 hour
  3. customAfter completion of the reaction
  4. customthe solvent was evaporated
  5. washthe obtained solid was washed with isopropanoyl
  6. filtrationcollected by filtration
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-608e5d76127747c3bd4153f4d1f2a387
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

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