Water → HCID 58577742, compound

HRID 587535Notes

Reaction equation

HRID 587535 reaction equation
Cl.[CH2:2]([O:9][C:10]1[CH:16]=[CH:15][C:13]([NH2:14])=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[C:18]1[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][C:21]([CH3:27])=[CH:20][N:19]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH2:2]([O:9][C:10]1[CH:11]=[CH:12][C:13]([NH:14][C:18]2[C:23]([N+:24]([O-:26])=[O:25])=[CH:22][C:21]([CH3:27])=[CH:20][N:19]=2)=[CH:15][CH:16]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 8183002-Chloro-5-methyl-3-nitropyridineHCID 27238314-Benzyloxyaniline hydrochloride

Product 1

HCID 58577742HCID 58577742, compoundYield 22.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 4-(benzyloxy)aniline hydrochloride (4.10 g) and 2-chloro-5-methyl-3-nitropyridine (3.0 g) in DMF (30 mL) was added TEA (7.27 mL) at room temperature, and the mixture was stirred at room temperature for 2 h. The mixture was heated to 60° C. After stirring at 60° C. overnight, K2CO3 (4.81 g) was added to the mixture. The mixture was heated to 100° C. and stirred at 100° C. overnight. The mixture was poured into water and the mixture was extracted with AcOEt. The combined organic layer was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography (dry charge, silica gel, eluted with 5%-30% AcOEt in hexane) to give N-[4-(benzyloxy)phenyl]-5-methyl-3-nitropyridin-2-amine (1.33 g) as a red solid. 1H NMR (300 MHz, DMSO-d6) δ 2.26 (3H, s), 5.11 (2H, s), 6.96-7.05 (2H, m), 7.29-7.54 (7H, m), 8.32-8.38 (2H, m), 9.78 (1H, s).

Workup

  1. temperatureThe mixture was heated to 60° C
  2. stirringAfter stirring at 60° C. overnight
  3. temperatureThe mixture was heated to 100° C.
  4. stirringstirred at 100° C. overnight
  5. extractionthe mixture was extracted with AcOEt
  6. washThe combined organic layer was washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by column chromatography (dry charge, silica gel, eluted with 5%-30% AcOEt in hexane)

Sources & evidence

ORD record
ord-c1c138473cad49b38197e74d05f2bd27
Source dataset
uspto-grants-2016_01
Patent number
US09226921B2

Reaction notes

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