Ethanolamine → HC Yellow No. 2

HRID 1886049Notes

Reaction equation

HRID 1886049 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[NH2:11][CH2:12][CH2:13][OH:14]>C(O)CCC>[N+:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:11][CH2:12][CH2:13][OH:14])([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 700EthanolamineHCID 69451-Chloro-2-nitrobenzene

Product 1

HCID 78637HC Yellow No. 2Yield 75%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

According to the procedure of B. Agai, et al., Tetrahedron, 32, 839, (1976), a solution of 1-chloro-2-nitrobenzene (50.0 g, 0.317 mol) and 2-aminoethanol (116.3 g, 1.904 mol) in nBuOH (400 mL) was heated under reflux for 6 hours. The mixture was concentrated, taken up in H2O, and extracted with ether. The organic phase was washed with brine, dried, and concentrated to give 43.1 g (75%) of an orange solid m.p. 78° C.

Workup

  1. temperatureunder reflux for 6 hours
  2. concentrationThe mixture was concentrated
  3. extractionextracted with ether
  4. washThe organic phase was washed with brine
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1f4484d822da47bfbade65dabe13df54
Source dataset
uspto-grants-1992_09
Patent number
US05149700

Reaction notes

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