3-Ethoxy-2-methyl-6-nitropyridine → 5-Ethoxy-6-methylpyridin-2-amine

HRID 847770

Reaction equation

HRID 847770 reaction equation
[CH2:1]([O:3][C:4]1[C:5]([CH3:13])=[N:6][C:7]([N+:10]([O-])=O)=[CH:8][CH:9]=1)[CH3:2]>C(O)C.[Pd]>[CH2:1]([O:3][C:4]1[C:5]([CH3:13])=[N:6][C:7]([NH2:10])=[CH:8][CH:9]=1)[CH3:2]

Participants

4

Reactant 1

HCID 128750163-Ethoxy-2-methyl-6-nitropyridine

Product 1

HCID 128750175-Ethoxy-6-methylpyridin-2-amineYield 90.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

18.2 g of the nitro compound obtained above was suspended in 300 ml of ethanol, which was reduced over 2 g of 5% palladium black under atmospheric pressure. After reaction, the catalyst was filtered off and the solvent was evaporated in vacuo. The residue was crystallized from benzene to obtain 13.8 g of 3-ethoxy-2-methyl-6-aminopyridine (Compound IV where R2 =C2H5), m.p. 98°-99° C.

Workup

  1. customAfter reaction
  2. filtrationthe catalyst was filtered off
  3. customthe solvent was evaporated in vacuo
  4. customThe residue was crystallized from benzene

Sources & evidence

ORD record
ord-7546caff650d435fac3441641d4fbc59
Source dataset
uspto-grants-1981_10
Patent number
US04293695

Linked notes

Loading…