Water → 2-((2-Aminophenyl)amino)ethan-1-ol

HRID 1886050Notes

Reaction equation

HRID 1886050 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[CH:10][C:5]=1[NH:6][CH2:7][CH2:8][OH:9])([O-])=O.Cl[Sn]Cl.O.[OH-].[Na+]>CCO>[NH2:1][C:4]1[CH:13]=[CH:12][CH:11]=[CH:10][C:5]=1[NH:6][CH2:7][CH2:8][OH:9]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 78637HC Yellow No. 2

Product 1

HCID 21140322-((2-Aminophenyl)amino)ethan-1-olYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

According to the procedure of B. Agai, et al., Tetrahedron, 32, 839, (1976), a mixture of 2-(2-nitroanilino)ethanol (43.1 g, 0.237 mol), SnCl2.2 H2O (267.0 g, 1.18 mol), and EtOH (400 mL), was heated under reflux for 4 hours. The mixture was cooled, made basic (pH8) with 2.5N NaOH, and filtered through Celite. The filtrate was concentrated to remove the EtOH and the aqueous phase was extracted with EtOAc. The combined extracts were washed with H2O and brine, dried, and concentrated. Recrystallization from EtOH gave 31.0 g (86%) of a brown solid m.p. 105°-106° C.

Workup

  1. temperatureunder reflux for 4 hours
  2. temperatureThe mixture was cooled
  3. filtrationfiltered through Celite
  4. concentrationThe filtrate was concentrated
  5. customto remove the EtOH
  6. extractionthe aqueous phase was extracted with EtOAc
  7. washThe combined extracts were washed with H2O and brine
  8. customdried
  9. concentrationconcentrated
  10. customRecrystallization from EtOH

Sources & evidence

ORD record
ord-08bb1e59f38047dc92ca8cb59ef45519
Source dataset
uspto-grants-1992_09
Patent number
US05149700

Reaction notes

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