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

HRID 724015Notes

Reaction equation

HRID 724015 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([CH3:11])[CH:5]=[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>>[CH3:11][C:6]1[CH:5]=[C:4]([CH3:12])[N:3]=[C:2]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][OH:22])=[CH:16][CH:15]=2)[C:7]=1[N+:8]([O-:10])=[O:9]

Participants

3

Reactant 2

HCID 669044-Aminophenethyl alcoholHCID 218755782-Chloro-4,6-dimethyl-3-nitropyridine

Product 1

HCID 218761062-{4-[(4,6-Dimethyl-3-nitro-2-pyridinyl)amino]phenyl}ethanolYield 80%

Conditions

Temperature
150 °C

Procedure

A mixture of 2-chloro-4,6-dimethyl-3-nitropyridine (step 2, 1.3 g, 7.0 mmol) and 4-aminophenylethyl alcohol (1.4 g, 10.2 mmol) was placed in a sealed tube and heated at 150° C. for 3 h. The reaction mixture was cooled and purified by flash column chromatography on silica gel eluting with hexane/ethyl acetate (2:1) to afford 1.6 g (80%) of the title compound as orange solids: 1H-NMR (CDCl3) δ 9.55 (1H, br.s), 7.57 (2H, d, J=8.4 Hz), 7.20 (2H, d, J=8.4 Hz), 6.52 (1H, s), 3.84 (2H, t, J=6.4 Hz), 2.85 (2H, t, J=6.4 Hz), 2.54 (3H, s), 2.42 (3H, s).

Workup

  1. customwas placed in a sealed tube
  2. temperatureThe reaction mixture was cooled
  3. custompurified by flash column chromatography on silica gel eluting with hexane/ethyl acetate (2:1)

Sources & evidence

ORD record
ord-44744867fd7f49a1bf98cd4570d37559
Source dataset
uspto-grants-2006_11
Patent number
US07141580B2

Reaction notes

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