Phenylethanolamine → HCID 57680910, compound

HRID 244144Notes

Reaction equation

HRID 244144 reaction equation
F[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[NH2:14][CH2:15][CH:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[OH:17].C(N(CC)C(C)C)(C)C>CCO>[OH:17][CH:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:15][NH:14][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 1000PhenylethanolamineHCID 679874-Fluoro-3-nitrobenzoic acidHCID 81531Diisopropylethylamine

Product 1

HCID 57680910HCID 57680910, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A flask, containing 4-fluoro-3-nitrobenzoic acid (8.00 g, 43.2 mmol) and 2-amino-1-phenylethanol (8.89 g, 64.8 mmol) dissolved in EtOH (80 mL), was purged with N2. Anh. N,N-diisopropylethylamine (19 mL, 108 mmol) was added and the reaction mixture was heated at reflux for 24 h. Later the reaction was cooled to rt and concentrated under reduced pressure. The solid residue was dissolved in EtOAc, washed (1 M aq HCl (3×), H2O (2×), brine), dried (Na2SO4) and evaporated to dryness to afford the title compound as a bright yellow solid; 1H NMR (400 MHz, DMSO-d6) δ 12.80 (s, 1H), 8.67 (t, J=5.2 Hz, 1H), 8.61 (d, J=2.0 Hz, 1H), 7.92 (ddd, J=0.4 Hz, 2.0 Hz, 9.2 Hz, 1H), 7.46 (d, J=8.4 Hz, 2H), 7.36 (t, 7.2 Hz, 2H), 7.28 (tt, J=1.2 Hz, 6.8 Hz, 1H), 7.18 (d, J=9.2 Hz, 1H), 5.89 (d, J=4.4 Hz, 1H), 4.91 (q, J=3.6 Hz, 1H), 3.72-3.63 (m, 1H), 3.53-3.45 (m, 1H). MS (ES+): m/z 285.1 (100) [MH+-18]; HPLC: tR=2.80 min (OpenLynx, polar—5 min).

Workup

  1. customwas purged with N2
  2. temperaturethe reaction mixture was heated
  3. temperatureat reflux for 24 h
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe solid residue was dissolved in EtOAc
  6. washwashed (1 M aq HCl (3×), H2O (2×), brine)
  7. dry with materialdried (Na2SO4)
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-58cd9370965c40ea8e08c58018b9e522
Source dataset
uspto-grants-2014_02
Patent number
US08653268B2

Reaction notes

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