2-(Dimethylamino)ethanol → HCID 58967008, compound

HRID 416253Notes

Reaction equation

HRID 416253 reaction equation
[F:1][C:2]1[C:8](F)=[CH:7][C:5]([NH2:6])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.[CH3:13][N:14]([CH3:18])[CH2:15][CH2:16][OH:17].[H-].[Na+]>N1C=CC=CC=1>[CH3:13][N:14]([CH3:18])[CH2:15][CH2:16][O:17][C:8]1[C:2]([F:1])=[CH:3][C:4]([N+:10]([O-:12])=[O:11])=[C:5]([NH2:6])[CH:7]=1

Participants

5

Reactant 3

HCID 79022-(Dimethylamino)ethanolHCID 24758Sodium hydrideHCID 1571514,5-Difluoro-2-nitroaniline

Product 1

HCID 58967008HCID 58967008, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A flame-dried round-bottomed flask was charged with 4,5-difluoro-2-nitroaniline (2.00 g, 11.49 mmol) and N,N-dimethylethanolamine. Pyridine (44 mL) was added followed by slow addition of NaH (60% in mineral oil, 965 mg, 24.1 mmol). The mixture was put under N2 atmosphere, stirred at rt for 16 h and quenched with H2O. Solvents were removed in vacuo and the residue was partitioned between H2O and EtOAc. The organic layer was extracted twice with HCl 1N, the combined acidic extracts were neutralized with saturated NaHCO3 to form a precipitate which was allowed to stand overnight, collected by filtration and purified by flash chromatography using MeOH/CHCl3 with increasing polarity (10:90 to 15:85) to afford the title compound 180 (1.30 g, 47% yield). 1H NMR: (CD3OD) δ (ppm): 7.76 (d, J=11.7 Hz, 1H), 6.53 (d, J=7.4 Hz, 1H), 4.19 (t, J=5.5 Hz, 2H), 2.84 (t, J=5.5 Hz, 2H), 2.37 (s, 6H). m/z: 244.2 (MH+).

Workup

  1. customquenched with H2O
  2. customSolvents were removed in vacuo
  3. customthe residue was partitioned between H2O and EtOAc
  4. extractionThe organic layer was extracted twice with HCl 1N
  5. customto form a precipitate which
  6. waitto stand overnight
  7. filtrationcollected by filtration
  8. custompurified by flash chromatography
  9. temperaturewith increasing polarity (10:90 to 15:85)

Sources & evidence

ORD record
ord-4444510d20ef4987965584947e8f6a3e
Source dataset
uspto-grants-2012_01
Patent number
US08088805B2

Reaction notes

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