Sodium Hydroxide → HCID 19363387, compound

HRID 850452Notes

Reaction equation

HRID 850452 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]1[CH:18]=[CH:17][C:8]([C:9]([O:11]CCCCC)=[O:10])=[CH:7][C:6]=1[NH:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>C(O)C>[CH3:3][O:4][C:5]1[CH:18]=[CH:17][C:8]([C:9]([OH:11])=[O:10])=[CH:7][C:6]=1[NH:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19363434HCID 19363434, compound

Product 1

HCID 19363387HCID 19363387, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethanol (3 ml) and a 1N aqueous sodium hydroxide solution (3 ml) were added to pentyl 4-methoxy-3-pentylaminobenzoate (500 mg, 1.63 mmol), and the mixture was refluxed under heating for 2 hours. Ethanol was evaporated under reduced pressure. Conc. hydrochloric acid was added to neutralize this solution, and the aqueous layer was etacted 3 times with ethyl acetate (5 ml). The organic layers were combined, washed 3 times with saturated brine (5 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 purif ied by washing with hexane to give 4methoxy-3-pentylaminobenzoic acid (356 mg, 71%) as colorless crystals.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 2 hours
  3. customEthanol was evaporated under reduced pressure
  4. additionConc. hydrochloric acid was added
  5. washwashed 3 times with saturated brine (5 ml)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationThe drying agent was filtered off
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe obtained crude crystals
  10. washby washing with hexane

Sources & evidence

ORD record
ord-8d2675c42a834e879991937959ef41ce
Source dataset
uspto-grants-2000_01
Patent number
US06017919

Reaction notes

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