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

HRID 419930Notes

Reaction equation

HRID 419930 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4](F)[C:3]=1[F:12].[CH2:13]([CH2:15][NH2:16])[OH:14]>C(O)C>[F:12][C:3]1[C:2]([F:1])=[CH:7][CH:6]=[C:5]([N+:8]([O-:10])=[O:9])[C:4]=1[NH:16][CH2:15][CH2:13][OH:14]

Participants

4

Reactant 2

HCID 700EthanolamineHCID 698711,2,3-Trifluoro-4-nitrobenzene

Product 1

HCID 579390192-[(2,3-Difluoro-6-nitrophenyl)amino]ethanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1,2,3-trifluoro-4-nitrobenzene (5.0 g, 28.2 mmol) and ethanolamine (1.72 g, 28.2 mmol) in 100 ml of ethanol is stirred over night at room temperature then at 70° C. for 5 hours. The reaction is concentrated to dryness and purified by silica gel flash chromatography using a gradient of 80/20 to 20/80 heptane/ethyl acetate providing an orange solid. Yield (3.8 g, 62%). 1H NMR (400 MHz, CDCl3) δ ppm 1.67 (t, J=5.08 Hz, 1H) 3.77-3.83 (m, 2H) 3.88-3.94 (m, 2H) 6.51 (ddd, J=9.77, 8.59, 7.03 Hz, 1H) 8.02 (ddd, J=9.77, 5.66, 2.34 Hz, 1H) 8.21 (s, 1H)

Workup

  1. concentrationThe reaction is concentrated to dryness
  2. custompurified by silica gel flash chromatography
  3. customYield (3.8 g, 62%)

Sources & evidence

ORD record
ord-47063d41b6c741059a112b33a4819e41
Source dataset
uspto-grants-2012_01
Patent number
US08093402B2

Reaction notes

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