Sodium Dithionite → 2-[(6-Amino-2-chloro-3-fluorophenyl)amino]ethanol

HRID 603115Notes

Reaction equation

HRID 603115 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([N+:9]([O-])=O)[C:3]=1[NH:12][CH2:13][CH2:14][OH:15].[O-]S(S([O-])=O)=O.[Na+].[Na+]>CO.O>[NH2:9][C:4]1[C:3]([NH:12][CH2:13][CH2:14][OH:15])=[C:2]([Cl:1])[C:7]([F:8])=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 24489Sodium DithioniteHCID 582984442-((2-Chloro-3-fluoro-6-nitrophenyl)amino)ethan-1-ol

Product 1

HCID 582984742-[(6-Amino-2-chloro-3-fluorophenyl)amino]ethanol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

2-[(2-Chloro-3-fluoro-6-nitrophenyl)amino]ethanol (5.52 g, 22.7 mmol) is dissolved in MeOH (40.0 mL). A premixed solution of Na2S2O4 (13.8 g, 79.5 mmol) in water (40.0 mL) is added to the first solution. The resulting solution is stirred for 5 minutes at 60° C. followed by 2 hours at room temperature. The solvents are evaporated, and the resulting residue is suspended in a saturated solution of NaHCO3 (40.0 mL). The aqueous phase is extracted 4 times with EtOAc (4×40.0 mL). The combined organic phases are dried with MgSO4, filtered and concentrated. The product is sufficiently pure by 1H NMR (2.07 g, 45%). 1H NMR (400 MHz, DMSO-D6) δ ppm 2.99 (m, 2H) 3.32 (s, 1H) 3.48 (t, J=5.57 Hz, 2H) 4.09 (s, 1H) 4.73-4.95 (m, 2H) 6.55 (dd, J=8.79, 5.66 Hz, 1H) 6.71 (t, J=8.89 Hz, 1H).

Workup

  1. waitfollowed by 2 hours at room temperature
  2. customThe solvents are evaporated
  3. extractionThe aqueous phase is extracted 4 times with EtOAc (4×40.0 mL)
  4. dry with materialThe combined organic phases are dried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-61f7058b94d049dba63eb22a009da4e8
Source dataset
uspto-grants-2011_03
Patent number
US07906654B2

Reaction notes

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