HCID 19979379, compound → HCID 19979371, compound

HRID 1461764Notes

Reaction equation

HRID 1461764 reaction equation
[CH:1]([C:4]1[C:9]([N+:10]([O-])=O)=[C:8]([CH:13]([CH3:15])[CH3:14])[CH:7]=[C:6]([O:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[N:5]=1)([CH3:3])[CH3:2]>O1CCCC1.[Ni]>[CH:1]([C:4]1[C:9]([NH2:10])=[C:8]([CH:13]([CH3:15])[CH3:14])[CH:7]=[C:6]([O:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[N:5]=1)([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 19979379HCID 19979379, compound

Product 1

HCID 19979371HCID 19979371, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

11.9 g of 2,4-diisopropyl-6-(4-chlorophenoxy)-3-nitropyridine are dissolved in 120 ml of tetrahydrofuran and, after the addition of 12 g of Raney nickel (suspended in ethanol), hydrogenated under normal pressure 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 1:3). 2,4-Diisopropyl-6-(4-chlorophenoxy)-3-aminopyridine is obtained in the form of a light-yellow crystalline powder, m.p. 86°-88° 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 1:3)

Sources & evidence

ORD record
ord-afb885509b6b481cb65d07877b8debe2
Source dataset
uspto-grants-1991_12
Patent number
US05077304

Reaction notes

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