2-[(2,3-Difluoro-6-nitrophenyl)amino]ethanol → 2-[(6-Amino-2,3-difluorophenyl)amino]ethanol

HRID 419931Notes

Reaction equation

HRID 419931 reaction equation
[F: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].[H][H]>C(OCC)(=O)C.C(O)C.[Pd]>[NH2:9][C:4]1[C:3]([NH:12][CH2:13][CH2:14][OH:15])=[C:2]([F:1])[C:7]([F:8])=[CH:6][CH:5]=1

Participants

6

Reactant 2

HCID 579390192-[(2,3-Difluoro-6-nitrophenyl)amino]ethanolHCID 178418361HCID 178418361, compound

Product 1

HCID 579390152-[(6-Amino-2,3-difluorophenyl)amino]ethanol

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-[(2,3-difluoro-6-nitrophenyl)amino]ethanol (3.8 g, 17.4 mmol) in 70 ml of ethyl acetate and 30 ml of ethanol is added 10% Pd/C (380 mg). The reaction is shaken under 50 PSI of hydrogen for 3 hours. The pressure is periodically adjusted to 50 PSI. The reaction is filtered through celite, rinsed with ethanol and concentrated. The resulting material is used without further purification in the next step. 1H NMR (400 MHz, CDCl3) δ ppm 3.17-3.27 (m, 2H) 3.68-3.78 (m, 2H) 6.38 (ddd, J=8.89, 4.69, 2.05 Hz, 1H) 6.61-6.70 (m, 1H)

Workup

  1. filtrationThe reaction is filtered through celite
  2. washrinsed with ethanol
  3. concentrationconcentrated
  4. customThe resulting material is used without further purification in the next step

Sources & evidence

ORD record
ord-938fcdea6a1243cd8b091fa94e5acc92
Source dataset
uspto-grants-2012_01
Patent number
US08093402B2

Reaction notes

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