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

HRID 850402Notes

Reaction equation

HRID 850402 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-29c9c9ef616746fc98c6eb33c34c7620
Source dataset
uspto-grants-2000_01
Patent number
US06017937

Reaction notes

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