Sodium Hydroxide → HCID 19977472, compound

HRID 1451090Notes

Reaction equation

HRID 1451090 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[NH:13][C:14](=[O:18])[CH:15]([CH3:17])[CH3:16])[C:5]([O:7]CC)=[O:6].[OH-].[Na+]>>[NH2:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[NH:13][C:14](=[O:18])[CH:15]([CH3:16])[CH3:17])[C:5]([OH:7])=[O:6]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 10610679HCID 10610679, compound

Product 1

HCID 19977472HCID 19977472, compoundYield 5.9%

Procedure

A sample of ethyl 3-amino-4-(2-methylpropionylamino)benzoate (2.30 g, 0.0092 mol) was suspended in 1N NaOH (13.80 mL, 0.0138 mol). After stirring for 24 h at room temperature, the reaction was then heated at 50° C. for 6 h. The reaction was filtered and the filtrate acidified with 1N HCl forming an orange precipitate. The solid was collected by filtration and thin-layer chromatographic analysis (SiO2, 9:1 ethyl acetate:methanol) indicated formation of a new lower-running spot (Rf =0.1). This material was recrystallized from N-butanol. The residue was collected by filtration and then suspended in ether. The product was filtered and dried in vacuo at acetone reflux to give 0.12 g (5%) of the title compound as a beige solid, mp 159°-160° C.

Workup

  1. temperaturethe reaction was then heated at 50° C. for 6 h
  2. filtrationThe reaction was filtered
  3. filtrationThe solid was collected by filtration and thin-layer chromatographic analysis (SiO2, 9:1 ethyl acetate:methanol)
  4. customThis material was recrystallized from N-butanol
  5. filtrationThe residue was collected by filtration
  6. filtrationThe product was filtered
  7. dry with materialdried in vacuo at acetone
  8. temperaturereflux

Sources & evidence

ORD record
ord-00216a7348a7445fae24bb6207ca51c2
Source dataset
uspto-grants-1997_02
Patent number
US05602277

Reaction notes

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