Hydrazine hydrate (1:1) → 5-Amino-2-(3-aminopropyl)-3-methylpyridine

HRID 34927

Reaction equation

HRID 34927 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH3:14])[C:7]([CH2:10][CH2:11][C:12]#[N:13])=[N:8][CH:9]=1)([O-])=O.O.NN>[Ni].C(O)C>[NH2:1][C:4]1[CH:5]=[C:6]([CH3:14])[C:7]([CH2:10][CH2:11][CH2:12][NH2:13])=[N:8][CH:9]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)2×HCID 198517775-Nitro-2-(2-cyanoethyl)-3-methylpyridine

Product 1

HCID 198517805-Amino-2-(3-aminopropyl)-3-methylpyridineYield 145.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalyst2×HCID 702EthanolSolvent2×

Procedure

Raney nickel (24 g) was added to a stirred solution under nitrogen of 5-nitro-2-(2-cyanoethyl)-3-methylpyridine (10.36 g) in ethanol (700 ml). Hydrazine hydrate (13.5 ml) in ethanol (30 ml) was added over 2.75 hr., followed by further additions of Raney nickel (15 g) and hydrazine hydrate (60 ml) over two days which included two periods of eight hours at 50° C. The solution was decanted off, filtered through a hyflo pad and concentrated to dryness to give a green oil (13 g). This oil was chromatographed on silica in ethylacetate/ethanol/0.880 ammonia 15:10:2 to give the title compound as an oil (8.14 g).

Workup

  1. customtwo periods of eight hours
  2. customat 50° C
  3. customThe solution was decanted off
  4. filtrationfiltered through a hyflo pad
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-e65b65387f754e1a8c83ddf37853aff1
Source dataset
uspto-grants-1988_08
Patent number
US04764519

Linked notes

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