2,6-Lutidine → 2-{4-[(5,6-Dimethyl-3-nitro-2-pyridinyl)amino]phenyl}ethanol

HRID 858409Notes

Reaction equation

HRID 858409 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([CH3:11])=[C:4]([CH3:12])[N:3]=1.[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][OH:22])=[CH:16][CH:15]=1.N1C(C)=CC=CC=1C>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:11][C:5]1[CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][OH:22])=[CH:16][CH:15]=2)=[N:3][C:4]=1[CH3:12]

Participants

6

Reactant 3

HCID 79372,6-LutidineHCID 669044-Aminophenethyl alcoholHCID 100811492-Chloro-5,6-dimethyl-3-nitropyridine

Product 1

HCID 218761712-{4-[(5,6-Dimethyl-3-nitro-2-pyridinyl)amino]phenyl}ethanolYield 37%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-chloro-5,6-dimethyl-3-nitropyridine (Godard, A.; Rocca, P.; Pomel, V.; et al. J. Organomet. Chem., 1996, 517, 25.; Rocca, P.; Marsais, F.; Godard, A.; et al. Tetrahedron Lett., 1993, 34, 2937., 3.3 g, 17.5 mmol), 4-aminophenylethyl alcohol (3.6 g, 26.3 mmol) and 2,6-lutidine (3.7 mL) in toluene (80 mL) was stirred under reflux temperature for 19 h. The mixture was diluted with ethyl acetate (100 mL) and washed with IN aqueous NaOH (50 mL) and brine (50 mL). The organic layer was dried (Na2SO4), and concentrated. Purification by flash column chromatography on silica gel eluting with hexane/ethyl acetate (1:1) to afford 1.8 g (37%) of the title compound as orange solids: 1H-NMR (CDCl3) δ 8.24 (1H, br.s), 7.68 (2H, d, J=8.6 Hz), 7.24 (2H, d, J=8.6 Hz), 3.88 (2H, dt, J=6.1, 7.6 Hz), 2.88 (2H, t, J=7.6 Hz), 2.49 (3H, s), 2.26 (3H, s), 1.43 (1H, t, J=6.1 Hz).

Workup

  1. temperatureunder reflux temperature for 19 h
  2. washwashed with IN aqueous NaOH (50 mL) and brine (50 mL)
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. concentrationconcentrated
  5. customPurification by flash column chromatography on silica gel eluting with hexane/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-d19b94ec82c64e5cbe786ff08cf41e6b
Source dataset
uspto-grants-2006_12
Patent number
US07148234B2

Reaction notes

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