HCID 19979377, compound → 6-Chloro-2,4-bis(1-methylethyl)-3-pyridinamine

HRID 1461766Notes

Reaction equation

HRID 1461766 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[C:5]([N+:11]([O-])=O)=[C:4]([CH:14]([CH3:16])[CH3:15])[CH:3]=1.[H][H]>O1CCCC1.[Ni]>[Cl:1][C:2]1[N:7]=[C:6]([CH:8]([CH3:9])[CH3:10])[C:5]([NH2:11])=[C:4]([CH:14]([CH3:16])[CH3:15])[CH:3]=1

Participants

5

Reactant 2

HCID 19979377HCID 19979377, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 199793736-Chloro-2,4-bis(1-methylethyl)-3-pyridinamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

30.0 g of 6-chloro-2,4-diisopropyl-3-nitropyridine are dissolved in 450 ml of tetrahydrofuran and, after the addition of 30.0 g of Raney nickel (suspended in ethanol), hydrogenated under a hydrogen pressure of 20 bar at from +30° C. to +35° C. The reaction mixture is filtered over diatomaceous earth and the filtrate is concentrated. The residue is purified by column chromatography on silica gel (eluant: ethyl acetate/hexane 3). 6-Chloro-2,4-diisopropyl-3-aminopyridine is obtained in the form of a clear crystalline powder, m.p. 53°-56° C.

Workup

  1. customat from +30° C. to +35° C
  2. filtrationThe reaction mixture is filtered over diatomaceous earth
  3. concentrationthe filtrate is concentrated
  4. customThe residue is purified by column chromatography on silica gel (eluant: ethyl acetate/hexane 3)

Sources & evidence

ORD record
ord-cdb7e2cb074443f4b345d32e6dc614cc
Source dataset
uspto-grants-1991_12
Patent number
US05077304

Reaction notes

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