Pyridine, 5-nitro-2-propyl- → 6-Propylpyridin-3-amine

HRID 1422073Notes

Reaction equation

HRID 1422073 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][CH3:12])=[N:8][CH:9]=1)([O-])=O.[H][H]>[Pd].C(O)C>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][CH3:12])=[N:8][CH:9]=1

Participants

5

Reactant 2

HCID 13860727Pyridine, 5-nitro-2-propyl-HCID 178418361HCID 178418361, compound2×

Product 1

HCID 138607306-Propylpyridin-3-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 5-nitro-2-n-propylpyridine (8.31 g, 50 mmol) and 400 mg 5% palladium on charcoal in 200 ml of ethanol was stirred in a hydrogen atmosphere until no more hydrogen was absorbed. The reaction mixture was filtered twice and the solvent was evaporated. The resulting oil was purified by kugelrohr destillation at 150° C. and high vacuum pressure. This gave 6.72 g (98%) of 5-amino-2-n-propylpyridine as a colourless oil. MS(GC): m/z 136 (M+). 1H-NMR (CDCl3, 200 MHz) δ: 0.83 (t, 3H); 1.60 (sext, 2H); 2.54 (t, 2H); 3.67 (br s, 2H); 6.81 (d, 2H); 7.91 (d, 1H).

Workup

  1. customwas absorbed
  2. filtrationThe reaction mixture was filtered twice
  3. customthe solvent was evaporated
  4. customThe resulting oil was purified by kugelrohr destillation at 150° C.

Sources & evidence

ORD record
ord-4bd3040589a04656b12109538a0ce3bf
Source dataset
uspto-grants-2000_06
Patent number
US06080754

Reaction notes

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