Sodium Bicarbonate → 2-[(2-Amino-6-bromophenyl)amino]ethanol

HRID 1991184Notes

Reaction equation

HRID 1991184 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-])=O)[C:3]=1[NH:11][CH2:12][CH2:13][OH:14].C(=O)(O)[O-].[Na+]>CO.O.[Cl-].[Cl-].[Cl-].[Ti+3]>[NH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[C:3]=1[NH:11][CH2:12][CH2:13][OH:14]

Participants

6

Reactant 2

HCID 516892Sodium BicarbonateHCID 112539952-[(2-Bromo-6-nitrophenyl)amino]ethanol

Product 1

HCID 112069902-[(2-Amino-6-bromophenyl)amino]ethanolYield 93%

Reagents, catalysts & solvents 3

HCID 10313229titanium(III) trichlorideCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 2-[(2-bromo-6-nitrophenyl)amino]ethanol (1.95 g, 7.5 mmol) in a mixture of methanol (30 mL) and water (15 mL) sodium acetate trihydrate (56 g) was added. To this mixture titanium trichloride (65 mL, as 15% solution in 10% aqueous HCI) was added drop-wise over period of 20 min. The resulting dark solution was allowed to stir for additional 2 h, and then carefully neutralized with saturated aqueous sodium bicarbonate. The solids were filtered off, and washed with ethyl acetate. The combined organic phase was washed with water and brine, dried over Na2SO4 and concentrated yielding 2-[(2-amino-6-bromophenyl)amino]ethanol as pale-yellow oil (1.61 g, 93%) that was used in the next step without further purification. MS (ESI) m/z: 231.01[M+H].

Workup

  1. additionwas added
  2. filtrationThe solids were filtered off
  3. washwashed with ethyl acetate
  4. washThe combined organic phase was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e63ccfe4cc1248a49c98b13a8a41c49c
Source dataset
uspto-grants-2010_01
Patent number
US07645784B2

Reaction notes

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