Triethylamine → HCID 19979376, compound

HRID 1461765Notes

Reaction equation

HRID 1461765 reaction equation
Cl[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.C(N(CC)CC)C>O1CCCC1.[Pd]>[CH:8]([C:6]1[C:5]([NH2:11])=[C:4]([CH:14]([CH3:16])[CH3:15])[CH:3]=[CH:2][N:7]=1)([CH3:10])[CH3:9]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 19979377HCID 19979377, compound

Product 1

HCID 19979376HCID 19979376, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

5.0 g of 6-chloro-2,4-diisopropyl-3-nitropyridine are dissolved in 100 ml of tetrahydrofuran and, after the addition of 2.75 g of triethylamine and 7.5 g of 5% palladium/carbon catalyst, hydrogenated under normal pressure at from +20° C. to +25° 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-3-aminopyridine is obtained in the form of a waxlike solid, m.p. 35°-39° C.

Workup

  1. customhydrogenated under normal pressure at from +20° C. to +25° 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-dc651fec52e5438bb3d33c8174d48c77
Source dataset
uspto-grants-1991_12
Patent number
US05077304

Reaction notes

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