Water → N-[4-(benzyloxy)phenyl]-4-methyl-3-nitropyridin-2-amine

HRID 572186Notes

Reaction equation

HRID 572186 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([CH3:11])[CH:5]=[CH:4][N:3]=1.Cl.[CH2:13]([O:20][C:21]1[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][CH:22]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(N(CC)CC)C.O>CS(C)=O>[CH2:13]([O:20][C:21]1[CH:22]=[CH:23][C:24]([NH:25][C:2]2[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([CH3:11])[CH:5]=[CH:4][N:3]=2)=[CH:26][CH:27]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 3453632-Chloro-4-methyl-3-nitropyridineHCID 27238314-Benzyloxyaniline hydrochloride

Product 1

HCID 58577297N-[4-(benzyloxy)phenyl]-4-methyl-3-nitropyridin-2-amineYield 63.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

A suspension of 2-chloro-4-methyl-3-nitropyridine (8.63 g), 4-benzyloxyaniline hydrochloride (13.0 g) and triethylamine (20.9 ml) in DMSO (150 ml) was stirred at 120° C. overnight. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was recrystallized from hexane/ethyl acetate to give the title compound (10.7 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was recrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-ba853adef5834168b1398bcd0ab07d49
Source dataset
uspto-grants-2015_05
Patent number
US09029388B2

Reaction notes

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