Hydrochloric Acid → 3-(2-Methoxybenzylamino)-2-phenylpyridine

HRID 1376817Notes

Reaction equation

HRID 1376817 reaction equation
[C:1]1([C:7]2[C:12]([NH2:13])=[CH:11][CH:10]=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.C([BH3-])#N.[Na+].[CH3:19][O:20][C:21]1[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=1[CH:23]=O>CO>[CH3:19][O:20][C:21]1[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=1[CH2:23][NH:13][C:12]1[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[N:8][CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 86582-MethoxybenzaldehydeHCID 27627843-Amino-2-phenylpyridineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 152327123-(2-Methoxybenzylamino)-2-phenylpyridineYield 56.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Under a nitrogen atmosphere, in a round-bottom flask were placed 500 mg (2.9 mmol) of 2-phenyl-3-aminopyridine, 10 mL of methanol and 1 g of 3A molecular sieves. The pH of the system was adjusted to ca. 4.5, using methanol saturated with HCl, and 190 mg (2.9 mmol) of sodium cyanoborohydride was added to the system. The pH of the system was adjusted to 4.5, 474 mg (3.5 mmol) of 2-methoxybenzaldehyde was added and the mixture was stirred at room temperature overnight. The mixture was filtered through (Celite®) and the filtrate was concentrated. The residue was partitioned between CH2Cl2 and saturated aqueous sodium bicarbonate, the layers were separated and the aqueous phase was extracted with three portions of CH2Cl2. The combined organic fractions were dried (Na2SO4) and concentrated with a rotary evaporator. The crude material was purified by flash column chromatography to obtain 475 mg of 3-(2-methoxybenzylamino)-2-phenylpyridine. Mp. 128°-129° C.

Workup

  1. customUnder a nitrogen atmosphere, in a round-bottom flask were placed
  2. additionwas added to the system
  3. additionwas added
  4. filtrationThe mixture was filtered through (Celite®)
  5. concentrationthe filtrate was concentrated
  6. customThe residue was partitioned between CH2Cl2 and saturated aqueous sodium bicarbonate
  7. customthe layers were separated
  8. extractionthe aqueous phase was extracted with three portions of CH2Cl2
  9. dry with materialThe combined organic fractions were dried (Na2SO4)
  10. concentrationconcentrated with a rotary evaporator
  11. customThe crude material was purified by flash column chromatography

Sources & evidence

ORD record
ord-52084417492c4f45b172a5786b3d42fb
Source dataset
uspto-grants-1997_09
Patent number
US05663349

Reaction notes

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