Pyridine → HCID 19363467, compound

HRID 850474Notes

Reaction equation

HRID 850474 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].C(Cl)Cl.N1C=CC=CC=1.[C:26](Cl)(=[O:31])[CH2:27][CH2:28][CH2:29][CH3:30]>O>[C:26]([NH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])(=[O:31])[CH2:27][CH2:28][CH2:29][CH3:30]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 61186Valeryl chlorideHCID 19363524HCID 19363524, compound

Product 1

HCID 19363467HCID 19363467, compoundYield 400%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Amino-3-pentyloxybenzoic acid (200 mg, 0.90 mmol), methylene chloride (5 ml) and pyridine (0.081 ml, 1.0 mmol) were mixed, and valeryl chloride (0.11 ml, 0.90 mmol) was added to this solution. The mixture was stirred at room temperature for 0.5 hour. Water was added to the reaction mixture, and the aqueous layer was extracted 3 times with ethyl acetate (5 ml). The organic layers were combined, washed with saturated brine (10 ml), and dried over anhydrous magnesium sulfate. The drying agent was filtered off and the filtrate was concentrated under reduced pressure. The obtained crude crystals were washed with hexane to give 4-pentanoylamino-3-pentyloxybenzoic acid (109.5 mg, 400%) as colorless crystals.

Workup

  1. extractionthe aqueous layer was extracted 3 times with ethyl acetate (5 ml)
  2. washwashed with saturated brine (10 ml)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationThe drying agent was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe obtained crude crystals
  7. washwere washed with hexane

Sources & evidence

ORD record
ord-f0f6dec37b6744daae4e17009bbb223c
Source dataset
uspto-grants-2000_01
Patent number
US06017919

Reaction notes

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