Pyridine → Methyl 3-pentanamidobenzoate

HRID 1939292Notes

Reaction equation

HRID 1939292 reaction equation
N1C=CC=CC=1.[NH2:7][C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=1)[C:11]([O:13][CH3:14])=[O:12].[C:18](Cl)(=[O:23])[CH2:19][CH2:20][CH2:21][CH3:22]>O>[C:18]([NH:7][C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=1)[C:11]([O:13][CH3:14])=[O:12])(=[O:23])[CH2:19][CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 1049PyridineHCID 61186Valeryl chlorideHCID 78274Benzoic acid, 3-amino-, methyl ester

Product 1

HCID 19171455Methyl 3-pentanamidobenzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To anhydrous pyridine (120 ml), methyl 3-aminobenzoate (5.00 g) was dissolved, and valeryl chloride (4.13 ml) was added while cooling on ice. The mixture was stirred at room temperature for 4 hours. Distilled water was added to the solution. The whole was extracted with ethyl acetate, washed with 5% sodium hydrogencarbonate aqueous solution and water, and dried over anhydrous sodium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography (Kieselgel 60=170 g, hexane/ethyl acetate=3/1) to obtain the above-captioned compound ([6]-(62)-90) (7.70 g) as a white solid.

Workup

  1. temperaturewhile cooling on ice
  2. extractionThe whole was extracted with ethyl acetate
  3. washwashed with 5% sodium hydrogencarbonate aqueous solution and water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was purified by silica gel column chromatography (Kieselgel 60=170 g, hexane/ethyl acetate=3/1)
  7. customto obtain the above-captioned compound ([6]-(62)-90) (7.70 g) as a white solid

Sources & evidence

ORD record
ord-a5677279c34641baadf2e2278419064c
Source dataset
uspto-grants-1997_12
Patent number
US05696118

Reaction notes

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