5,6-Dimethyl-2-methoxy-3-nitropyridine → 3-Amino-5,6-dimethyl-2-methoxypyridine

HRID 489262Notes

Reaction equation

HRID 489262 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([N+:11]([O-])=O)[C:5]([O:9][CH3:10])=[N:6][C:7]=1[CH3:8]>O1CCCC1.[Pd].CO>[NH2:11][C:4]1[C:5]([O:9][CH3:10])=[N:6][C:7]([CH3:8])=[C:2]([CH3:1])[CH:3]=1

Participants

5

Reactant 1

HCID 222664775,6-Dimethyl-2-methoxy-3-nitropyridine

Product 1

HCID 109972273-Amino-5,6-dimethyl-2-methoxypyridineYield 98%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

5,6-Dimethyl-2-methoxy-3-nitropyridine (1-013-06) (2.56 g) was dissolved in tetrahydrofuran (41 mL), and to the reaction mixture was added a suspension of 5% palladium on carbon (450 mg) in methanol (41 mL), and then the catalytic reduction was carried out. After 3 h, catalyst was filtered off, and the filtrate was evaporated under reduced pressure to give 3-amino-5,6-dimethyl-2-methoxypyridine (1-013-07) (2.096 g, 97.9%, m.p.: 56-58° C.) as a blackish brown crystal.

Workup

  1. additionto the reaction mixture was added
  2. filtrationcatalyst was filtered off
  3. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-ac3dc1c05f0c40b986582765ec577bb7
Source dataset
uspto-grants-2005_12
Patent number
US06977266B2

Reaction notes

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