Ethanolamine → 2-((2-Chloro-3-fluoro-6-nitrophenyl)amino)ethan-1-ol

HRID 419947Notes

Reaction equation

HRID 419947 reaction equation
[Cl:1][C:2]1[C:7](F)=[C:6]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:4][C:3]=1[F:12].[CH2:13]([CH2:15][NH2:16])[OH:14].CCN(CC)CC>CCO>[Cl:1][C:2]1[C:3]([F:12])=[CH:4][CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[C:7]=1[NH:16][CH2:15][CH2:13][OH:14]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 8471TriethylamineHCID 2230803-Chloro-2,4-difluoronitrobenzene

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Chloro-1,3-difluoro-4-nitrobenzene (5.37 g, 27.7 mmol), ethanolamine (1.69 g, 27.7 mmol) and Et3N (2.80 g, 27.7 mmol) are stirred in EtOH (40.0 mL) at room temperature for 2 hours. The solvent is then evaporated, and the resulting residue is suspended in EtOAc (50.0 mL) and washed with 0.5 N NaOH (50.0 mL). The aqueous phase is extracted 4 times with EtOAc (4×50.0 mL). The combined organic phases are dried with MgSO4, filtered and concentrated. The product is purified by flash chromatography on silica gel, eluting with mixtures of heptane and EtOAc (5.53 g, 85%). 1H NMR (400 MHz, DMSO-D6) δ ppm 3.39 (dd, J=10.55, 5.27 Hz, 2H) 3.53 (t, J=5.47 Hz, 2H) 4.89 (s, 1H) 6.89 (dd, J=9.37, 8.01 Hz, 1H) 7.19 (t, J=4.69 Hz, 1H) 8.01 (dd, J=9.47, 5.96 Hz, 1H).

Workup

  1. customThe solvent is then evaporated
  2. washwashed with 0.5 N NaOH (50.0 mL)
  3. extractionThe aqueous phase is extracted 4 times with EtOAc (4×50.0 mL)
  4. dry with materialThe combined organic phases are dried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe product is purified by flash chromatography on silica gel
  8. washeluting with mixtures of heptane and EtOAc (5.53 g, 85%)

Sources & evidence

ORD record
ord-c855d8e080594cd49319df575d597fd4
Source dataset
uspto-grants-2012_01
Patent number
US08093402B2

Reaction notes

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