3-Aminopyridine → 3-(4-Geranyloxybenzoylamino)pyridine

HRID 342666Notes

Reaction equation

HRID 342666 reaction equation
[H-].[Na+].[NH2:3][C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1.[CH2:10]([O:20][C:21]1[CH:29]=[CH:28][C:24]([C:25](O)=[O:26])=[CH:23][CH:22]=1)/[CH:11]=[C:12](/[CH2:14][CH2:15][CH:16]=[C:17]([CH3:19])[CH3:18])\[CH3:13]>O1CCCC1>[CH2:10]([O:20][C:21]1[CH:22]=[CH:23][C:24]([C:25]([NH:3][C:4]2[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=2)=[O:26])=[CH:28][CH:29]=1)/[CH:11]=[C:12](/[CH2:14][CH2:15][CH:16]=[C:17]([CH3:19])[CH3:18])\[CH3:13]

Participants

5

Reactant 3

HCID 100093-AminopyridineHCID 24758Sodium hydrideHCID 123615004-Geranyloxybenzoic acid

Product 1

HCID 867535613-(4-Geranyloxybenzoylamino)pyridineYield 32.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium hydride(0.74 g) and 3-aminopyridine(0.87 g) were stirred in tetrahydrofuran(30 ml) for 1 hour while being cooled with ice. 4-geranyloxybenzoic acid(2.54 g) and N,N'-carbonyldiimidazole(1.65 g) was stirred in tetrahydrofuran(10 ml) for 30 minutes at room temperature and the mixture was added to the former reaction mixture. After being stirred for 20 minutes at room temperature, the reaction mixture was concentrated under a vacuum. The residue, with water added thereto, was extracted with ethyl acetate. The extract was dried over sodium sulfate anhydride and then concentrated under a vacuum. The residue was purified by silica gel column chromatography (chloroform:methanol=20:1). The resulting solid was recrystallized from n-hexane/ethyl acetate, thereby yielding 1.05 g of the aimed compound.

Workup

  1. temperaturewhile being cooled with ice
  2. additionthe mixture was added to the former reaction mixture
  3. concentrationthe reaction mixture was concentrated under a vacuum
  4. additionThe residue, with water added
  5. extractionwas extracted with ethyl acetate
  6. dry with materialThe extract was dried over sodium sulfate anhydride
  7. concentrationconcentrated under a vacuum
  8. customThe residue was purified by silica gel column chromatography (chloroform:methanol=20:1)
  9. customThe resulting solid was recrystallized from n-hexane/ethyl acetate

Sources & evidence

ORD record
ord-35ddcdabcf344f2ab9564f191d414c50
Source dataset
uspto-grants-1999_01
Patent number
US05859032

Reaction notes

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